Tetrahedron Letters 1991: Vol 32 Index

188 Pages·1991·87.6 MB·English

Tetrahedron
Letters
The International Journal for the Rapid Publication of Preliminary
Communications in Organic Chemistry
Founded jointly by Sir Robert Robinson and R. B. Woodward
Chairman of the executive board of editors for Tetrahedron publications
Sir Derek Barton Texas A&M University U.S.A.
SUBJECT AND AUTHOR INDEX
NUMBERS 1-52 1991
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TETRAHEDRON LETTERS
The International Journal for the Rapid Publication of Preliminary Communications
in Organic Chemistry
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Chairman: Professor Sir Derek Barton, FRS, Department of Chemistry. Texas A&M University, College Station,
PN 77843-3255, USA (FAX 409 S45 4719)
Professor J. E. Baldwin, FRS, Dyson Perrins Laboratory, Professor A. Nickon, Department of Chemistry. The Johns
Oxford. England (FAX: [phone]) Hopkins University, Baltimore. MD 21218. USA
Professor D. L. Boger, Department of Chemistry. The Scripps (FAX: | 4105168420)
Research Insutute. La Jolla, CA 92037, USA Professor W. D. Ollis, FRS, University of Sheffield. Sheffieia
(FAX: [phone]) S3 7HF. England (FAX: [phone])
Dr S. G. Davies, Dvson Perrins Laboratory. Oxford, England Professor G. Ourisson, Centre National de la Recherche
(FAX: [phone]) Scientifique, Centre de Neurochimie. 5 rue Blaise Pascal,
Professor L. Ghosez, Laboratoire de Chimie Organique de 67084 Strasbourg. Cedex. France (FAX: [phone])
Synthese, Université Catholique de Louvain. Place L. Pasteur Professor T. Shioiri, Faculty of Pharmaceutical Sciences,
1. B-1348 Louvain-la-Neuve. Belgium (FAX: [phone]) Nagova City University, Tanabe-dori, Mizuho-ku, Nagova
Professor S. Ito, Faculty of Pharmaceutical Sciences. 467, Japan (FAX: [phone])
Tokushima Bunri University. Yamashiro-cho, Tokushima Professor W. Steglich, Institut fur Organische Chemie und
770, Japan (FAX: [phone]) Biochemie der Universitat Bonn, D-5300 Bonn 1. Gerhard-
Professor A. R. Katritzky, FRS, Department of Chemistry, Domagk-Strasse 1. Germany (FAX: [phone])
University of Florida, Gainesville, FL 32611, USA Professor H. H. Wasserman, Department of Chemistry, Yale
(FAX: [phone]]99) University. PO Box 6666. New Haven. CT 06511. USA
Professor N. K. Kochetkov, N. D. Zelinsky Institute of (FAX: | 203 432 9990)
Organic Chemistry. Academy of Sciences USSR, Leninsky Professor W. T. Wipke, Thimann Laboratories. University of
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Chemical Sciences, University Plain, Norwich NR47TJ,
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Editor Tetrahedron Organic Chemistry Series: Professor J. E. Baldwin FRS, Dyson Perrins Laboratory, Oxford. England
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. D. Bartlett, Fort Worth. TX A. Eschenmoser, Zurich M. L. Mihailevic, Belgrade k. B. Sharpless, La Jolla. CA
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D. J. Cram. Los Angeles. CA V. A. Koptyug, Novosibirsk P. Potier, Gif-sur-Yvette P. von Ragueé Schlever, Erlangen
P. Deslongchamps, Quebec M. Lahav, Rehovat S. K. Pradhan, Bombay Y. Wang, Shanghai
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Tetrahedron Letters
Subject Index 1991
Corrigenda Acetals cyclonona—1 ,2—dien—4—one ethy-
André B., Boyer B., Lamaty G.., (+)-exo—brevicomin, synth using lene —, acid—catalysed cycloaddn
Roque, J.—P.: 32, 1881 (1991): transketolase, 4835 to 1,3-dienes, 6473
correction to Table 1: time di- (—)-endo—1 ,3—dimethyl—2,9—diox- D—myo-inositol D-camphor
mension in rate constant units is abicyclo[3.3.1]nonane, beetle 2,3—acetal, synth trisphosphate
to be min™ rather than sec™', pheromone synth, 2223 and bisphosphate, 6167
4056 1,3-dichloroacetone —, cyclization dieth yl— of prop—2—ynal, but—
Bajwa J.S. and Anderson R.C.: 31, to cyclopropenone acetals, 1339 3—ynal, 2—meth ylbut—3—ynal,
6973 (1990): paragraph omitted 1,3-diol acetonide, cleavage to addn of tributyltin—copper
from end p. 6975 is given, 1758 enol ether by trimethylsilyl tri- lithium reagents, 6333, 6337
Barili P.L., Berti G., Catelani G. flate, stereochem and mech, °C dihydrox ylation of unsat spiroace-
and D’A ndrea F.: 32, 959 (1991): labelling, 7223
tals, stereosel, 4049
two lines omitted with details of
2,2’—spirobi(tetrah ydropyran) dimethy] tartrate —, with dialkylbo-
compds 8 tetraacetate, 9, and 17
derivs in synth open—chain mil- ron bromides and cuprate, dias-
diacetate, 2692
bemycin analogs, 1719 tereosel alcohol formation, 5453
Goulet M.T. and Boger, J.: 31,
2,3-dih ydro—2,3—dihydroxy—S—vi- dioxaspiro[2.4]nonanes, exocyclic
4845 (1990): rapamycin and al-
nylfuran cyclohexanone -, cy- glycal oxides, 4035
lied structures (1, 3, 5, and in
cloaddn to benzoquinones, 1519 formation using sulfonylated char-
Scheme following 5) corrected,
2—bromocycloalk—2—enone ethy- coal as catalyst, 413
6454
lene —, organocuprates from, furfural —, 4~metallo—derivs, 903
Huang Y., Mullah N., Sopchik
605, 609
A.E., Arif A.M., Bentrude W.G.: fused —, 3a,6a—dihydrofura-
2—deox y—1—-O-—butyldimethyisi-
32, 899 (1991): substitute table no[2,3—b]furan systems by
of NMR parameters with correct lyl sugars as glycosyl donors, Ma(OAc);-promoted addns to
2079
compound numbers, 3900 dihydrofurans, 7107
3+pent—4—enyl)}-ortho—benzoqui-
Hudlicky M. and Merola J.: 31, glyoxal mono—acetal, [4+2]-cy-
none mono—dimethylacetal, in-
7403 (1990): configurations of cloaddn to 2—methylpen-
formulae of starting materials tramol [4+2]-cycloaddn, 6583 ta~1,3-diene, 1723
7-oxabicyclo[2.2. 1 }heptan—2-one,
and intermediates corrected, hydrolysis —, in sterically switched
5—exo,6—exo-—isopropylidene-
3134 ionophore, 35
dioxy-—, reaction with diazome-
Iwamoto K., Fujimoto K., Matsuda ionone type C;3 acetals from
thane, 1637
T. and Shinkai S.: 31, 7169 quince (Cydonia oblonga)
(1990): revised Table 1, to cor- Ol—alkox yalkylation of silyl en- brandy, 753
rect Cs9CO, entry, 830 olates by, 2043 ketene silyl —, activation in Mukai-
Luheshi A.—B.N., Salem S.M., Ol—phenylthio—acylals, from Pum- yama reaction by 10—methylacri-
Smalley R.K., Kennewell P.D., merer rearr of vinylic sulfoxides, dinium perchlorate, 2405
Westwood R.: 31, 6561 (1990): 6973 meso/dl diphenylsily! —, from en-
m.p. and yield of iminophospho- acylketene —, chiral, diastereose- antiomeric alcohols, 3651
rane 10 corrected; also statement
lectivity of addns to, 461, 465 mono—camphor — of myo-inositol,
in 32, 2521 (1991), 4056
ambracetal, epi-8—ambracetal, synth D-myo-inositol 1—phos-
Orfanopoulos M., Elemes Y. and synth using C=O protection, 765 phate, 4031
Stratakis M.: 31, 5775 (1990):
bicyclic, synth trandamycin A, monothio-, from aldehydes using
correction to ene adduct struc- 1749 Si reagents, 467
ture, 2
bromoacetaldehyde — to ketene — N-acyl-N,O-acetals, stereosel
Prapansiri V. and Thornton, E.R.:
by solid—liquid PTC base elimi- reactions with 2—(trimethylsily-
32, 3147 (1991): reference add-
nation, 1539 loxy)furan, 3795
ed, misprint corrected, 6044 catalysis of hydrolysis by polymer- naphtho[3,2-b]pyran—2-one,
Santaniello E., Ferraboschi P. and
ised micellar surfactants, 1881, bridged, reduced diacetal, part
Grisenti P.:31, 5657 (1990): on p.
corrigendum, 4056
5659, information on PFL-cata- structure of paspalicine, 1381
lysed hydrolysis of racemic ace- chiral — of N—anisyl Ol—keto—imi- oxidation of alkylidenemalonates
tate 4b added, sentence and reac- nes, diastereosel addn of ester to B,B -dimethoxyalkylmalonic
tion scheme corrected, 430 enolates, synth BHactams, 7563 esters, 799
Vallgarda J. and Hacksell U.: 32, chiral spiro— from 1,3,5—pentane- pivalaldehyde — and lactic acid,
5625 (1991): structure of Oppol- triols and (—)—menthone, 1219 1,3-—dioxolan—4—one from, effect
zer’s camphorsultam corrected, cleavage by chloroborane—dime- of acid catalyst, 1441
7136 thylsulfide, 3719 seleno—, unsaturated, acid—cata-
conversion into N—methyl amides lysed cyclization, 105
or lactams by N—methy] p—nitro- silyl ketene —, conjugate addn to
benzenesulfonylox yamine, 2429 enones catalysed by LiClO,
Abzymes cyclic ketals, reduction v0B e hy- 4665
see Antibodies
droxyalkyl ethers by BH3.SMe2 spiro—, in calyculin structure, syn-
and TMS-triflate, 1095 thetic operation of, 1609
Tetrahedron Letters
spiro—, phyllanthocin, asymmetric Acylation Alcohols
synth, 1613 2-acyl—3—hydrox ymethylquino- 1,2-dihydro—1—arylbenzocyclobu-
spiro—, breynin B, revised struc- lines by intramol acyl transfer,
ten—1-ols, synth via aryl O-li-
ture, nmr, 6847 2171
thioarylmethyl ketones, reduc-
spiro—5/7—, formation, structure cobalt(II) chloride catalysed — of
tion by Et3SiH/TFA, 2171
by x-ray, 2253 anisole, radical pathway, 5179
stereosel synth spiroketal subunit c titive benzoylation of ani- 2,2-difluoro—homoallyl—, Ol-chlo-
of calyculin, 4855 sole and mesitylene on montmo- ro—O,0.-difluoroalkene addn to
stereospecific fragmentation of rillonite, 1561
ketones, 1069
bridged B-hydroxyalkyl—, lac- enzymic, of 2-amino-BHiactam 3,3—difluoroallyl —, reaction with
tone synth, 5585 deriv, 1621 DAST forming (Z)-trifluorome-
synth, chiral epoxidation, of homolytic, of ferrocene, mecha- thyl alkenes, 5963
(E)-S—hydrox ypent—3—enal di- nism, 4993 3—bromohomoallylic —, synth,
methyl acetal, 5717 intramol — of O—sulfonyl anion by 6749
TiCl.—mediated coupling to
anhydride residue, 4457 (t-halofluoroalkyl—, O—halofluo-
B—keto-esters, —amides, 3635 of glycosylamines by
roalkenyl—, synth by electrore-
TiCl,—mediated reaction with 3—acyl—S—methyl—1 ,3,4—thiadia- ductive couplings, 6567
buta—2,3—dienyltrimethylsilane, zole—2-thione, 1557
aliphatic —, using lipase and vinyl
4509
laurate, 7021
see also Aminals, Thioacetals
allenic, propargylic —, by reaction
of aldehydes with pentaorgano—
stiboranes, 6579
Adamantanes allyl —, from trialkeny! boranes by
Acetogenins 2,2-dibromo-—, Br—Li exchange,
B-Zn group transfer, 2449
(+)-muricatacin and epi—, synth and reaction of adamantanone
allyl —, quinoline synth by Pd-ca-
(4S,5R)— from L—glutamic acid, with 7,7—dilithionorbornane,
talysed coupling to o-iodoani-
7539 2951
itrabin, jetein, tetrahydrofuran 2,4—dimeth ylmethano—2,4—didehy- line, 569
allylic — by reductive Smlz—pro-
—Hiactones from Annona dro—, synth, reaction with elec-
moted carbonyl—alkyne cou-
cherimolia seeds; \aherradurin, trophiles, 1655
pling, 4921
otivarin, 6133 adamantylidene-, singlet oxygen-
ation, 863 allylic tert—, Ol-iodo—epoxides
alkylidene-, electron—transfer
from, using PhI(OAc)>2/I/hV,
reactions induced by aminium 7493
Acidity salts, 117 allylic, Ru—catalysed isomn to satd
kinetic — of 1—protons of 1,5—anhy- di—1—adamantylchloromethane, aldehydes, ketones, 3039
dro—4,6—O-benzylidene—2,3-—di- dechlorination by BuLi in hex-
B—alkylhomoallyl-, YO-epoxy-
os ro—D—hex-—2-enitol, ane, 2203
Ikyl—, chiral synth via
mono-, di-—, tri-azulenylmethyl tenolides, 371
cations, pXKg+ values, 773
B-iodoall ylic —, Grignard addn to
B—iodo-enals, 5329
Addition reactions
2,3—dimeth ylbut—2-ene adducts nitro—, improved synth, 3225
Acids with N—phenyl-1 ,2,4—triazo- nzylic —, reaction with allenylsi-
see Carboxylic acids, Sulfonic line—3,5—dione, product dichoto-
lanes giving dihydronaphtha-
acids, etc. my, 2667 lenes and spiro—trienones, 2327
alkyllithium reagents to
catalytic arylation of allyl alcohols
2—(1-naphthyl)-2-oxazolines,
to styryl alcohols and to B- aryl-
2095
ethyl aldehydes and ketones, °
Acridines by nucleophilic aromatic addn, of
10—methylacridinium perchlorate 2—phenyl—1—tosylaziridine 2121
as catalyst in Mukaiyama reac- anion, 1299 chain mech photo—addn to fluoro—
tion, 2405 dinitrogen tetroxide to 1,2—dime- olefins, 251
connected to octathymidylic acid thylcyclohexene, 1711 chiral allylic — by Li-V—methyle-
with alternating P=S and P=O hydrochlorination of 1 ,3—buta- phedrine promoted addn of 1-al-
groups, 2497 diene, surface—catalysed, 3461 kenylzinc bromides to alde-
glyfoline synth, 1,6—dihy- hydrochlorination of olefins with/ hydes, 5777
droxy—2,3,4,5—tetrame- without solid—phase catalyst; chiral homoallylic, by Ti-catalysed
thoxy—10—methylacridone, 1541 Markownikov/anti—M. addn to aldehyde-ene cyclizations, 6571
photoreduction 10—methylacridi- 1—methylcyclohexene, 3705 chiral, enantiosel protonation of
nium ion by Ph3P in Michael addn of amines to nitro— ketone enolates, 4729
MeOH/H20, 1047 cycloalkenes, 1363 cobalt—catalysed conversion allylic
thiazolo—fused acridones, synth, 39 photochemical, of MeOH to phe- alcohols to rearranged N—allyl
thiazolo[5,4—-a]acridines, 11-chlo- nylcyclopropanes, 173 acetamides, 6965
ro—, 1l—amino—, —11(6H)-ones,
config inversion by Mitsunobu
synth, nmr, 6709
reaction, p-nitrobenzoate as in-
coming nucleophile, 3017
conversion of prim and sec C-OH
Aggregation
into C-SPh using Ph2S2/BusP at
Acylals sec—alkyllithiums, influence of —
10 kbar, 4155
see Acetals on addn of ethylene, 3111
coumaryl, coniferyl, sinapyl, synth
from allylphenols, 2475
Tetrahedron Letters
diastereosel secondary — synth us- Q—bromo”, in homo—Pictet—Spen- enolisable, condensation with Me
ing aldehyde dimethy] tartrate acetoacetate, CoCl> catalysed,
gler cyclizations, 619
acetals, 5453 1663
enyne alcohols, reduction by Rieke O-trifluoromethyl—OtB—unsaturat- from primary carboxamides with
Zn to dienyl alcohols, 299 ed acids from, by Reformatsky Li bis— or tris—(dialkylami-
enzymic synth opt active cis— reaction, 339 no)aluminum hydrides, 6903
epoxy—alcohols, 3043 OB-epoxy—, from photosensi- fumaraldehyde, 1)?— and T)4-iron
tised oxygenation of phytol,
imethylsilyl-OLp—e xy- carbonyl complexes, 7259
6551
Le diastereosel my 5789; y-oxy-}-ketoaldehydes, intramol
reactons forming chiral allylic OB-epoxyaldehydes, chiral, addn
pinacol reduction by Sml>, Tish-
tert—alcohols, 5793 of Li enolates, 5345
chenko lactone formation by
homoallyl—, by addn crotyl-Mo addition of methyl—metal reagents
complexes to aldehydes, 1271 to 2—(tetrah ydrofuran—2—yl)ace- SmI,OBu', stereochem, 5097
glyoxal derivs, hetero—Diels—Alder
homoallylic — synth by BF; pro- taldehyde, 1937
addns to 1,3-dienes, 1723
moted addn allyl(cyclopentadie- addition to crotyl—-Mo complexes,
nyl)iron(IT) dicarbony]l to alde- homoallyl alcohols from, 1271 homoallylic ethers from by silyl—
modified Sakurai reaction, 4779
hydes, 3001 alcohol oxidation in presence of
homoallylic —, by cyclization oxidisable thioacetal unit, 4631 hydrogenation of, ([l—hydridodich-
epoxy—olefins, 243 aldeh ydo—sugars, with ethox ycar- romium decacarbonyl)” cataly-
homoallylic, stereocontrolled bonyl methylene triphenylphos- sis, 1199
synth, 1073 phorane forming 2-deoxy—6—for- ketol group transfer to, enzyme—
homoallylic, synth using indium, myl—3,6—anh ydro—hexo- mediated, 5085
allyl halides, and carbonyl com- no—1,4—lactone dimethyl acetals, methyl 5—formylpent—2—ynoate,
pounds, 7017 7473 reaction with 4—metallofurans,
hydroxy group protection, pivaloy- arabinose bis—acetonide, condn 903
laminobenzyl derivs, DDQ or with vinyl thioether, 1809 monothioacetals from, using Si
hydrogenolysis to cleave, 4019
aromatic —, [SiCl,;—promoted reac- methodology, 467
isoleucine, valine, extension to tion with acrylonitrile, N—aryli- nitriles from by Cu(I])—promoted
B—hydrox y-6—aminoacids, 2395 dene 3—aminopropenal, 5421 ammonoxidation, 1007
oxidation by dioxiranes, mech of, aromatic, addn to Li enolates in pinacol cyclization 1,5/6—dials by
533 soln and solid phase, 1535 Smlb>, cis—1,2-diols, 1125
oxidation to aldehyde in presence aromatic, with bis(aroylmethyl) piperonal, 3,4—dimethox yphthalal-
of thicacetal unit, 4631 sulfoxides forming chalcones, dehyde, condn with N-BF;-
oxidation to aldehydes aromatic 7469 complexed t—amine Ol—anions,
N-oxides catalysed by RuO2-te- asymm Ag(I)-catalysed condensa- 3221
tramesitylporphyrin, 7435 tion with Me cyanoacetate, oxa-
reaction with (S,S)—bis—p—toluene-
primary, by Ru-catalysed hydro- zoline formn, 2799
sulfinylmethane, asymm induc-
formylation—reduction of olefins,
B-alkoxy-, C-trimethylsilylvinyl- tion, 3695
505
cuprate addn to, 857 reaction with allenic, propargylic
propargyl —, amino—dehydroxyla-
pentaorgano—stiboranes, 6579
tion in Nicholas reaction, 2137 B-hydroxy-, two-step allylation
reaction with arsoniosilylated
propargylic —, reduction to allyl — forming methylenecyclohexanes,
by LAH/MaOMe, 2339, 2343 oB-unsat enals forming furans,
steroidal homoallylic, oxidation to benzaldehyde formed in radical 2913
enediones by PrsNRuO,, N—me- elimination of benzyloxy group, reaction with boron enolate in
thylmorpholine oxide and ultra- 2017
B—hydroxy—}-amino amide
sound, 3201 benzaldehyde, stereoselectivity of synth, 2453
sulfinylation by sulfonyl cyanides addn to chiral allylstannanes, reaction with diphenyl 2—bromoal-
and DBU, 2585 453 lylboronate, synth 3—bromoho-
tert— synth, (S)-prolinol as chiral carboxy—allylation, Pd—catal ysed moallylic alcohols, 6749
auxiliary via 2—acyloxazolidines, Sn—mediated, in O—methy- regeneration from semicarbazones
2919
lene—Y—butyrolactone synth, 225 using CuCl2.2H20 in acetoni-
tertiary —, dehydration by
catalytic arylation of allyl alcohol trile, 5829
BF3.Et,0, 6489
satd — by Ru—catalysed isomn al-
tetrahydropyrany] ethers, conver- to B-arylethyl aldehydes, 2121
lylic alcohols, 3039
sion into bromides and iodides,
chiral O—-hydroxy—, synth from stereoisomerism of BF3 com-
1081
Ol—ketoaldehydes using (S)-pro- plexes, and reaction with (l-al-
linol as chiral auxiliary, 2919 koxyallyl stannanes, 2867
citronellal, enantiosel reduction of synth by hydrogenolysis acyldime-
by bakers” yeast, 2643 thylsilanes, 457
Aldehydes conversion into ethynyl group us- synth by intramol Heck reactions
ing (EtO)2PO.CHN3 , 2343 involving allylic alcohols, 6113
1,2-diol diacetates from, using
BrCH,OCOMe and Sml)>, 2433 cycloaddn to 5—alkox y—2-aryloxa- synth perfluoroalkylacetaldyedhe s
zoles, Lewis—acid catalysed, by radical addn Rp-SAr to enol
2,3-dihydrobenzaldehydes, synth
from prenal enolates and enals, 6911 ethers, 3385
4495 diastereosel addn to 1 ,3-dithiane synth secondary amides from using
2,6-dibenzylbenzaldehyde, other trans—di—oxide anion, 7743 nitriles and SiCl3I, 1825
2,6—disubst aldehydes for por- diastereosel condn with Y—(trime- thioacetalization using FeCl; on
phyrin synth, 1703 thylsilyl)all ylboranes, 3029 silica, 2259
3-formyloxyaldehydes, chiral electroreductive coupling with ha- TiCl.—mediated reaction with
synth from D-glucose, D-xylose, lofluoro—compounds, products of buta—2,3—dienyltrimethylsilane,
367 further reduction, 6567 4509
Tetrahedron Letters
Vilsmeier—Haack formylation of tandem with amination of electro- (R)-reticuline to salutaridine, en-
glucal, —— ethers, 3875 ilic olefins using Ti(NR2)4, zymic oxidation by pig liver cy-
see also 71 tochrome P-450, 3675
transannular [-—promoted aldol cy- 100(-hydrox ymethylsparteine, qui-
clization of 5—-formyl—2-iodo—
nolizidine — from Genista sessili-
Slactone, 6227 folia, struct, 5915
13-azabicyclo[7.7.0.0' “Jhexade-
Aldol reactions cane skeleton synth, towards
SS 3—di(benzylme- fawcettimine, serratinine, Lyco-
thyl)aziridine, reaction Li en- Alkaloids podium —, 6219
olate with PhCHO, 2533 (+)- frog — indolizidine 209B, 19-—hydrox ytubotaiwine, indole
aldehydes with Li enolate of N.N- synth, 5889 Strychnos —, synth, abs config,
dimethylglycine ester, stereosel — 1787
in presence of Et3B, 5521 (+)-coccinine, montanine, pancra- alexines, pyrrolizidine —, synth
aromatic aldehydes, addn to Li en- cine, Amaryllidaceae —, synth, from sugar lactones, 5517
7079
olates in soln and solid phase, aspidochibine, 3-oxo—14,15-dehy-
1535 (+)-corytensine, (+)-egenine, drorhazinilam, indole — from As-
asymm Ag(I)-cata 7 -—o f Me
O—hydrox ybenzyl tetrah ydroiso- pidosperma quebracho blanco,
isocyanoacetate, quinoline — synth, 3221 4949
asymmetric, chiral boron reagents
(+)-8-coniceine, indolizidine -, asymm synth of intermed to
in, 1749
synth, 5051 (—)}-koumine, (—)-taberpsychine,
Baylis—Hillman reaction, kinetics
(—}-koumidine, 3895
and mechanism, 5611 (+)}-deoxypseudophrynaminol,
bornylaminesulfonic acid sultam frog — analog, synth, 7641 line sponge —, reticulatine
as chiral auxiliary, 61 A, B, fascaplycin B, ms, nmr,
(+)-epilupinine synth by transan-
structs, 1843
boron—mediated —, in two—direc-
nular cyclization of 10—mem-
tional polypropionate chain line tunicate —, eudistomi-
bered lactam, 5709
synth, 7601 dins E, F, proton, C—13 nmr,
(+)-iso—-oxy—skytanthine, synth,
chiral, of t-butyl bromoacetate 3539
with aldehydes, 2857 3051 benzylisoquinolines, synth papav-
diastereoselective — of (+)-O-methyljoubertiamine synth erine, norreticuline derivs by
thian—4—one, polypropionate using cyclohexadienyl Fe(CO),* modif Pomeranz—Fritsch, 1775
synth, 5369 complex, 1291 canadine, tetrahydropalmatine, en-
dimer-— and tetramerization of ace- Ceggeticntn C, frog —, synth, zymic reduction protoberberines,
tophenone promoted by diethyl- 487
zinc, structure of dynopinacol, castanospermine, 6—acetami-
6037 (+)-sedridine, piperidine —, synth, do-6—deoxy-, synth, 719
4371
enantioselection in condensations catharanthine, photoactivated oxi-
using camphor—derived oxazoli- (+)}-septicine, (+)ylophorine, dation, CN-addn, C16-C21
done boron chelate, 5563 synth via dihydropyridone in- cleavage, 3035
enzyme-catalysed, 7,8—dideoxy termeds, 5919 codeinone derivs, photo-rear-
—4—octulose 1—phosphate, 3159 (+)-vasicine, pyrrolo—quinazoline, rangements, 7499
Evans — of O-aminoaldehydes, de- synth via 2,3—dioxopent—4—-enoic cuanzine, indole —, stereosel synth
pendence of stereochem on reac- ester, 7131 racemic, 4491
tant proportions, 7287 (+)}-carnegine, tetrah ydroisoquino- discorhabdin C, sponge alkaloid,
intramolecular, forming 13—mem- line —, synth, 6861 synthetic approach, 2035
bered ring of tetronolide, 4925 (+)-castanospermine, indolizidine eupolauramine, synth of precursor,
Mukaiyama reaction, catalysed by -, synth, 4147 4883
10—methylacridinium perchlo- (+)-epiaustraline, (—)-epialexine, flavocorylene, synth by Westphal
rate, 2405 pyrrolizidine —, synth, 5513 condensation, 7575
N,O-dimethylacetamide Li en- (+)4ycoridine, phenanthridone -, girolline, sponge —, diastereosel
olate, addn to C=O compds, synth, 4525 synth, 1419
2525 (+}-pinidine, piperidine —, synth, glyfoline synth, 1,6—dihy-
O-silylketene O,S—acetals, with 5029 droxy—2,3,4,5—-tetrame-
Co—complexed and uncom- (—)-antirhine, synth using thox y—10—methylacridone, 1541
plexed trimethylsilyl—propynal, branched sugar lactone, 4483 hippadine, indolo—isoquinoline -,
7553 (—)-cannabisativene, chiral synth, synth by Pd—catalysed cycliza-
pyruvate—pyridinecarbaldehydes, 1649 tion, 3859
6—amino—6—deox y—[7]} yclo- (—)-cocaine, pear. pathway to hydrastine synth, methylenation of
dextrin as enzyme model, 1207 — —pyridyl )butanoate, diol, 2461
retro—, in synth fused cyclohepta- imeluteine, 6—azafluoranthene -,
nedicarboxylic acid, 4177 ee, At EES synth, 5277
reverse —, synth hydroazulene- synth, 7233 indole, synth cadambine from se-
diones from silyloxy—bicy- (—)-heliotridane, (—)-isoretroneca- cologanin, 1987
clo[3.3.Ojoctene — ketene add- nol, pyrrolizidine —, synth via isonitramine, synth by intramol
ucts, 6011 T—allyl iron tricarbonyl com- Sy2’ lactam enolate alkylation,
stereosel anti—, synth hydroxye- plex, 7119 1577
thylene, erythro—dihydroxyethy- (—)—nupharamine, (+)}-3-epinupha- kimbasine A and B, sponge norses-
lene dipeptide isosteres, 6507 ramine, synth, 4325 terterpene —, pmr, cmr, 2347
stereoselective, of B-oxoboronic (-—)-slaframine, indolizidine —, en- litebamine, phenanthrene — from
esters, 1507 antiosel synth, 6469 Litsea cubeba, 4169
substd benzaldehydes with pinaco- (—)-solenopsin B, piperidine - magniflorine, indole — from Hame-
lone dibutylboron enolate, sub- an fire ant, enantiosel synth, lia magniflora, isol, pmr, cmr,
stituent effects, 5239 41 5153
Tetrahedron Letters
manzamine A, synth pyrro- Alkeny]l halides N-—methylation of aminoacids dur-
lo[2,3—/Jisoquinoline portion, ing hydrogenolytic deprotection
1-iodoalk—4—enes from 2—(Ol—ace-
6481 in methanol—acetic acid, 7463
toxyalkyl) tetrahydrofurans,
monocrotaline, dehydro-, nucleo- 3059 nucleophilic, O-tetralols to Ot-al-
side alkylation by, 927
alkox ycarbonylation usin kyltetralins, 2087
N-nornitidine, benzo[{c}phenanthri- HCO2R/NaOR/PdCl¢ )2,
of sec amines at C(QL) via y-
dine —, synth, 5757 4705
droxyalkyl N—oxides OxaZo-
paraherquamide, chemical modifi-
allylic fluorides, stereochemn of
lidines, 1443
cation of vinyl ether moiety, epoxidation, 6355
2437, substn at oxindole N, 2441 of re acetals,
B-iodoalkenoic esters, aldehydes, 1
pictamine, quinolizidine — from tu-
of pentadienyl iron tricarbony] cat-
nicate Clavelina picta, 3667 iodoallylic alcohols, 5229
ions, by Cu-Zn complex re-
prianosins C and D, 1,7—phenan- dehalogenation and cyclization to
agents, 113
throline derivs from sponge C=O groups using
Prianos melanos, structure revi- Bu3Sn.SiMe3/R4NX, 6139 reductive —, RgN—CH2—1-benzo-
sion, 1227 pentafluoroallyl iodide, hexafluo- triazolyl into R3N-CH>-R’ (R =
rubrolone, tropone — from mould, ropropene, reactions with me- allyl, alkyl), using BiCl,/AI/RBr,
synth AB ring ion, 7643 thine bases, malononitrile, 4595 4247
silicine, ervatamine indole —, synth thiols from using Me2RSiSLi, regioselective — of 2—methyl—1-si-
2189 ylallyl carbanions, 2879
(+)-20-deethyl analog, 5413
triple condn with allenes and car-
strychnochromine, revised tetrahy- trans—Ol-stannyl epoxides, stereo-
banions, 1795
droquinoline structure, nmr, x- chem of reductive — by organo-
ray, 4295 vinyl chloride — acetylene cross— Li reagents, 6305
coupling, PdClo(PhCN)>.Cul in
ungeremine synth by radical cycli-
piperidine, 6109
sation, 65
verruculotoxin, fungal —, synth,
1417 Alkyl halides
vincadifformine, tabersonine, oxi- bromides, cobaloxime-—catalysed
dative acylation by TFAA at t— coupling to styrene, 6273
amine centre, 5081 Alkylation di—1—adamantylchloromethane,
yuehchukene, indole —, synth, 1,3,2—diazaphospholidine 2—ox- mech of dechlorination by BuLi
1045 ides, at P, 6297 in hexane, 2203
2,3-alkanedi(cyclohexyl, isopro- gem-dihaloalkanes, Co—catalysed
pyl)imines, via Ol-anions, 3879 diethylaminocarbonylation, 781
9-trimethylsilyl—9, 10—dih ydroan- perfluorohexyl-, ring-opening to
1—bromo-tridecafluoro—2—octa-
thracenes, anion formation and
Alkanes rearr, synth 9,9—dialkyl dihy- nol, no addn of PhMgBr, 3047
(SRS-9S)-5,9-dimethyi-heptade- thiols from using Me2RSiSLi,
droanthracenes, 3969
cane and —pentadecane, synth of alkylation, nucleophilic, by dialkyl 2189
moth pheromones, 2643
zirconocenes promoted by
catalytic hydroperoxide oxidation, KOBu-, 3895
manganese cluster for, 1153 aromatics on clay, reversal of me-
Alkynes
sitylene and toluene reactivities,
1—phenylthio-, Pd—catalysed hy-
2901
Birch reductive — of aromatic ke- drostannation, 5047
tones, 1929 2’-deoxygenation of 2’—alkynyl-
Alkenes C-—methylation of phenol via Man- arabinonucleosides, 6003
(Z)trifluoromethyl—, synth by nich base, 2083 acetylenes from 3,4—disubst isoxa-
action of DAST on 1,1-difluo-
calix[4]arenes, conformation and zolin—S—ones with
ro—1—alken—3—ols, 5963
solvent effects, 2675 NaNO>/FeSO,, 5321
(—trifluorometh yl-Ol—methox y- cyclopentadecanone and 15—hexa- alkynyl phenyliodonium tetrafluo-
carbonyl-, from aldehydes by decanolide, 1027 borates, addn of H—Hal, synth
Reformatsky reaction, 339 diastereosel — of chiral binaphthol
alovinyliodonium salts, 4753
catalytic hydroperoxide oxidation, monocrotonyl esters and ana- alkynyl—Cu(CN)Li, reaction with
manganese cluster for, 1153 logs, 7281
ICH>2Zal forming dienes, etc,
halofluorination, BugNH>F3 as electroreductive — of cyclohepta- 1855
fluoride source, fluoroalkene trienes, 1051 alkynyl—I*—Ph BF,-, iodide reduc-
synth, 1215 Eschweiler—Clarke methylation of
tion to alkynes, 4753
radical addn to iodomethy!] phenyl polyamines, fragmentation reac-
alkynylcarbenes, rearrangements,
sulfone, 3259 tions during, 7755 983
synthesis using 2—(alkylsulfo- Friedel-Crafts, 1,4—di(dodecahe- arylalkynylalanes, benzylidenecy-
nyl)benzothiazoles, 1175 dryl)benzene, 5259 clopentanes from 1,4—tert-dihal-
trisubst olefin synth by selective intramol lactam enolate alkylation, ides and, 521
cis or trans hydrostannylation of 1577
B-hydroxy—, metal—catalysed
disubst alkynes, 7535 methylation 6—amino—8—pyrinone
ring-opening of epoxides by Li
see also Olefins derivs, regiochem, 97
acetylides, 6617
methylation, Eschweiler—Clarke,
bis(arylsulfonyl)acetylenes, synth,
of B—aminopropionic acid, Diels—Alder reactions, 217
imeth ylammonio—betaine, bis—t—butylsulfonylacetylene,
Alkenylation 847 transformations of Diels—Alder
Mitsunobu C— of o—nitroaryl ace- adducts from, 4579, 4583
nucleophilic, Of-tetralols to Ol-al-
tonitriles, 7195 but—2—yne—1,4—diol, conversion
kenyltetralins, 2087
N,O-dimethylation of intractable or
hydroxy—amide, 2395 286
Tetrahedron Letters
but—3—yn—1—ol, carboxylation and see also Cycloalkynes, Diynes, En- (t-ethoxycarbonyl-, Pd(II)}-Sna-
elaboration to B—keto—d-valero- ynes, Enynones, Y namines mediated butyrolactone synth
lactone, 3063 from aldehydes, 225
chiral ethynyl! sulfoxides, addn of allylic acetates with phenylthio—
nucleophiles, 4907 group adjacent, regiosel reaction
dialkylaminopropynoic esters, ni- Alkynyl halides with silyl enol ethers, 4311
triles, cycloaddn to 2~arylide- 1,4—dibromo—2~—byunte , conver- anionic, of chiral imines by allyl—
neindane—1 ,3—diones, 4051 sion into heterocyclic di— and Cu reagents, 1367
diethylacetals of prop-2-ynal, poly—ynes, 2883, 2887 bis(hydrox ymethyl)acetaldehyde,
but—3—ynal, 2—methyl- 1,4—dichloro—2—butyne, reaction asymm induction in — to 2—hy-
but—3—ynal, addn of tributyltin— with RZnBr in presence of drox ymeth ylhex—5—ene-1 ,3-diol
copper lithium reagents, 6333, CuCN.2LiBr, formn of 2,3-dial- derivs, 6939
6337 kyl—1 ,3—butadiene, 2865 C— of N-(diphenylmethylene)gly-
cine ester by LDA/allylic iodide,
dimethyl acet ylenedicarbyloatxe ,
7203
reaction with [1,2,3]triazo-
lo[1,5-a)pyridinium ylids, 4977 catalytic de—, Ir—catalyst for
Allenes double bond isomerization,
electrophilic —, addn to triphenyl-
phosphine in microemulsion, 1—diphenylphosphinoyl-, 1—phe- Me3NO/OsO, (cat) for cleavage,
2615 nylsulfinyl—, and 1—phenylsulfo- 7369
indium for — of aldehydes, ketones
ethyl propiolate, radical [2+2+2] nyl— 1-(@-iodoalkyl)—, radical
in aqueous media, 7017
cycloaddn to acrylic esters, 5101 cyclizations, 3659
monomenthyl cyclopentane—
from aldehyde using 1-trimethylsilyl—1-tosyl—, alkyl-
1,2-dicarboxylate, C—of Li
(EtO)2PO.CHN2 , 2343 Li addn, reaction with SOo, thio-
enolate, stereochem, 4541
halo-, by action of (Me3SiO)» and phene formation, 3867
nucleophilic reactivity of allylsa-
CuX>, or ZnX> on 1-alkynes, alkoxy—, Pd—catal ysed hydrostan-
marium complexes, 629
2169 nation, 1187
Pd—catalysed — at Me of 6,6—diMe
heterocyclic azine ligands, ethy- allene substitute in cycloaddns,
fulvene, 5247
nyl—substituted, 757 O-methylene-B-lactones, 7033
radical, of O—haloesters by Allyl—
hydroformylation of B—alkyna- alleneacetic acid esters by reduc-
SnBusz, 27
mines, pyrroles from, 1093 tion by s—Bu2Cu(CN)Liz of
sequential 2— and 1-electron — us-
hydrostannylation, selectively cis pent—2-en—4—ynoate esters, 7229
ing 3—phenylthio—2~—(trimethylsi-
or trans, in trisubst olefin synth, allenylsilanes, reaction with benzyl
lylmethyl)propene, 843
7535 alcohols giving dihydronaphtha-
intramol addn of nitronate anion lenes and spiro—trienones, 2327
to, 1363 B—methoxycarbonylvi nyl—, synth
Me tert—propargyl carbonates, by Pd—cat reaction Me tert—pro-
synth Me 1,2,4—triene—S—carbox- parey! carbonates with Me acry-
Aluminum compds
ylates by Pd—cat reaction with ate, 3397
1—alkenyldiisopropylalane, reac-
Me acrylate, 3397 bromo—, copper—catal ysed ami-
tion with protected glycosyl
methyl! 5—formylpent—2—ynoate, nolysis to propargylamines, 7471
fluorides, 2199
reaction with 4—metallofurans, bromoboration of —, in situ reac-
alkyl-, alkyl—fluoro—alanes, cata-
903 tion of (2—bromoallyl )dibromo-
lysts for hydrofluorination of an-
o-alkynyl—-Ol-diazoacetophenones, borane with anisole, 6749 hydrothymidine, 2091
Wolff rearrangement with cycli- buta—2,3—dienyltrimethylsilane in alkylalanes, reaction with azodi-
zation, 5923 synth 2—Ol—hydroyaxl - formic mono—amide mono-ester,
phenylacetylene, catalytic conver- kyl)-1,3—butadienes, 4509 3079
sion into O—phenylpropionic carbopalladation of in steroid arylalkynylalanes, benzylidenecy-
synth, 915 clopentanes from 1 ,4—tert-dihal-
acid, 1769
carbopalladation, synth dienyl ides and, 521
reaction with bis(2,4,6—triisopro-
pylphenyl)borane, 6239 etoesters, malonate esters, determination of lithal purity/con-
795 centration, 4309
silylethynyl ydrox yalkyl ke-
chiral synth and ozonolysis of alle- diaryloxy—Al—methyl, Lewis acid
tones, synth and stereosel reduc-
nyl alcohols, 5713 catalysts for S—alkox yoxazole—
tion by DIBAL-H, 2219, 2223
cyclonona—1 ,2—dien—4—one ethy- aldehyde cycloaddn, 6911
synth from halides using triorga-
lene acetal, acid—catalysed cy- diethyl cyanoalane, reaction with
no-Tl reagents, 2255
cloaddn to 1,3—dienes, 6473 chiral B-ketosulfoxides, 3195
terminal —, 4—biphenylyldialkylsi-
intramol Ag*—catalysed addn of Li bis-, tris—(dialkylamino)alumi-
lyl group for protection and
N-H group to O-(2,3-butadie- num hydrides, reduction of pri-
formn crystalline derivs, 3787
nyl) carbamates, 4—vinyl—-2—oxa- mary amides to aldehydes, 6903
terminal —, hydrozirconation,
zolidinone synth, 6359 trialkylalanes, alkylation and deox-
transmetalation and alkylation, optical resolution of allenes by ygenation of 2—-lithio—2-triphe-
synth trans—alkenes, 5647
chromatography on cellulose nylsilyloxirane by, 2783
terminal, Pd-catalysed coupling to
triacetate, 7225 trichloride in oligomerization of
bis—enol triflate, 1449, 1453
phenylallenes, dye—sensitised pho- acyl chlorides, 2153
terminal, Pd—catalysed coupling to
to—ox ygenation, 1859 trimethylalane, ring-opening of
trifluoroacetimidoyl iodides,
sulfonyl-, intramol cycloaddns of, chiral epoxides by, 1059
1459
1351 trimethylalane catalyst in reaction
trifluoromethyl-, synth from
of Grignard reagents with chiral
loro-BH trifluorome- sulfinamides, 5885
thyl)}-enals, 3071 trimethylalane, reaction with chiral
vinyl chloride — acetylene cross— Allylation 2-p—tolylsulfinyl cyclohexa-
coupling by PdCl2(PhCN)>.Cul 1,4—oxathian—2—one, — at S and nones and cyclopentanones,
in piperidine, 6109 rearr of ylid, 335 3191
Tetrahedron Letters
tristrimethylsilylalane, vinylsilanes N-allyl—, aza—Claisen rearr to ally- N-acyl-N sulfonyl—, part struc-
from, 855 lacetonitriles in presence dehy-
ture in retrosulfonamido peptide
tristrimethylsilylalane, synth of drating agent, 199 analog, 6779
acylsilanes from acylthiopyri- N-methyl-, from ketones via ace-
tryptophan, N,N -ethylidenebis-,
dines and, 4929 tals using N—methyl p—nitroben-
vinyl diisobutyl alanes, dibutyl zenesulfonyloxyamine, 2429 identity with “contaminant 97”,
991
methyl vinyl alanates, conver- N-propargy] nicotinamides, isoqui-
sion into vinyl trialkyl stannanes, noline—1—carboxamides, intra-
7647 mol cycloaddn, synth of isoindo-
vinyl—Al reagents, Pd—catalysed lin—1—ones, benz[e]isoindo-
lin—3—ones, 5481
cross—coupling Ol-iodo—enones, Amination
a mg er ng mm
4453 asymmetric — of carboxylic acids,
‘om phthalimides, conveys base
5349
stability, 3301
by trisyl azide, of chiral 3~(subst—
oligo-, intramol hydrogen—bond-
— 2-oxazolidinone,
ing, MM studies, 3613, 3617
optically active, by enzymic hy-
Amides electrophilic BOC-, of organome-
drolysis of nitriles, 1343
2,3-epoxy—4—oxo-—7, 10—dodeca- tallic species, 2359
primary —, reduction to aldehydes
dienamide, enantio-—, stereo—sel with Li bis— or tris—(dialkylami- enolate — by di-t—butyl azodifor-
synth from D—tartaric acid, 6771 mate, 6851
no)aluminum hydrides, 6903
nucleophilic, using Ti(NR2)4, 2371
G-aryloxy-By-epox y—amide, reduction to alcohols by
of chloronitrobenzene using micro-
synth in Passerini reaction, 3807 Sml>/base, 3511
wave heating, 5251
replacement in dipeptides by imi-
0t-chloroacetamides, N—vinylic, tropone to 2—aminotropone by hy-
dazoline, 2277
cyclization by Bu3SnH, 1725 drazine, 1051
secondary, from nitriles and alde-
-fluoro—tert—, by enolate fluori- hydes using SiCl3I, 1825
nation, 1779
stereosel synth of (2R,4S)—4—ami-
oB-unsaturated tert—,, reductive no—2—methylpentanamide derivs,
dimerization by SmlI2, 6557 5749
Amines
succinamides, by [3,3]-rearr of
Off-easetarated, radical addn to,
(+)}+trans-1 ,2-diamino—1 ,2—dime-
07 N.N -diacylhydrazine dienolates,
thylcyclohexane, synth, 1711
acetanilide nitration by NO/O3, 4517
(S)}-N—methyl—1—phen yl—2-piperi-
ortho-selectivity, 6591 trichloro—diacetanilides, synth, se-
dinoethylamine, (S-M ), chi-
acetanilides from nitroarenes, Ru— lective para—dechlorination,
ral ligand for cuprate reactions,
catalysed reductive acylation by 7191
3973
AcOH and Me formate, 4917
1,2—diamines from glyoxal bis(di-
aminoacid — from enol esters, 5359
phenylmethylimines), chiral
B-hydroxy-, reduction to Pent
Amidines from bis(0l—phenylethylimines),
noalcohols by LiAIH4, 1901 asymmetric 1—alkylation of 5865
By-unsat -, synth from B-(die- 1,2,3,4tetrah ydroisoquinolines 1 ,4—diazabicyclo[2.2.2]}octane,
thoxyphosphory])propionic acid, via chiral formamidine derivs, (+)}-+trans—2,3—diphenyl-, synth,
6231 5501; racemisation of 1—chiral 4853
derivs on lithiation, 5505; mech 2,2,2—trifluoro—1—phenylethyl-,
borohydride reduction of O—meth-
of alkylation, 5509 synth, resolution, 987
yl—p—keto—amides, effect of
chiral imidazolines from cyclic 7—-(amino— and subst ami-
ZnCl>, CaClo, MnCl on stereo- sulfates using, 999 no)-5,6,7,8—tetrah ydroquino-
chem, 6147
cyclic amidinium salts, synth, 5031 lines, synth, 6789
carboxamide protection by trityl
form-, 4—fluoropyrimidines from
group, 739 Ql-anions of N-BF3;—complexed
(t-trifluoromethylalkyl ketones tert—, condn with aldehydes,
diastereomeric 2,2,2—trifluo-
ro—1—phenylethylamides, !9F and, 2467 3221
shifts, 987 Qt-arylethylamines, enantiosel
dieth ylbenzamides, ortho-lithi- synth, 7175
ation in synth saccharin ana- Amido—ketones Qlithio+—, generation, use,
logues, 7179 3—aminoindan-1—ones, alkoxy-, 1975
formation from acids using lipases,
synth by Friedel-Crafts cycliza- alkoxycarbonylation of — using
2763 di-2-pyridyl carbonate and alco-
tion acylamino-f—arylsuccin-
from acids, activation by hol, 4251
ic - 6327
NNN .N -tetrameth yl-O-succi- anilines, 2—halo—, quinolin—4—ones
nimidouronium fluoborate, 1157 a using acetylenes/CO/Pd(0),
Hofmann rearr of — using
PhI(OCOCF3)2, 4249 Aminals aromatic, reaction with formalde-
lipase—catalysed synth from esters cyclic O-allyl ketene —, 3—subst hyde and cyclopentadiene, 7099,
and amines, 761 piperidones, pyrrolidones, by 7103
benzyl transfer in benzylamine on
malonamides, N,N,N ,N —tetrae- Claisen rearr, 4199
clay, redox process, 303
thyl—, from gem-dihalides, CO, glyoxal chiral monoaminal mono—
benzylamines, conformation in va-
NHMe? Co catalyst, 781 dimethylhydrazone, asymmetric
por phase by MRES, 3945
N-(Ql-silylbenzyl)amides, Si—shift (—aminoaldehyde synth, 1171 Co-—complexed allyl propargyl
and azomethine ylid generation, N-acyl-N’ —benzyloxycarbonyl-, amines by Nicholas reaction,
5813 Hg**—promoted cyclization to 2137
N-allyl acetamides, Co—catalysed 2,5—disubst imidazolidin—2- from nitroalkanes by reduction
synth from allylic alcohols, 6965 ones, 1971 with SmI, 1699
Tetrahedron Letters
Heck cyclization N—-(2-haloal- (E)-O-(2-phenylcyclopropyl)gly- L-arginine, triple—N—protection as
lyl)cyclohex—3—enylamines to cine, asymm synth, 541 urethanes, via silyl derivs, 6025
2-azabicyclo[3.3.1]non—6—enes, (S)-3 ,5-dihydrox yphenylglycine, L-diphenylalanine, L-(9-fluore-
1695 synth, 2663 nyl)glycine, synth by alkylation
Hofmann rearr of amide using 11-aminoundecanoic acid as pep- of benzophenone imine of glycyl
PhI(OCOCF3)2, 4249 tide sequence surrogate in cyclic camphor sultam, 6547
homoallylic primary —, sterocon- L—-N©-hydroxyarginine, synth,
polypeptide ANF, 7735
trolled synth via 2—isoxazolines
2—amino-6,6—pentamethyle- N-—15—labelled, 875
with 5—(diphenylphosphinoylal-
neoct—4-enedioic acid, disulfide L—pyroglutamic acid, asymm pyr-
kyl) subst, 4171
mimetic, synth, 7203 rolidin—2—ones from, 1379
hydroformylation of p—alkyna- 3—amino—2-arylpropanoic acids L—pyroglutamic acid, synth ant
mines, pyrroles fan from benzylic lithiation of N-pi- venom pyrrolines, pyrrolidines
Michael addn to nitro—cycloal- valoylphenylethylamine, 1963 from, 7521
kenes, 1363 3—phenylisoserine, asymm synth L—valine incorporation into isobu-
o-iodoaniline, quinolines by Pd-
via B-lactam, 3151 tyric, methacrylic acids in beetle,
catalysed coupling to allyl alco-
4—dimeth ylamino—2,3—dihy- 4849
hols, 569
drox y—5S—methox ypentanoic mixed carbonic anhydrides, boro-
polydi/trimethylmienneis, linear
and cyclic, fragmentation reac- acid, stereosel synth calyculin hydride reduction, 923
tions during Eschweiler—Clarke fragment, 5983 N~2,4,6—trinitropheny])aminoa-
methylation, 7755 5—aminydroox— y-46-p-hehnyl - cids, photolysis, 5823
primary (E)-allylic -s, synth from hexanoic acid, stereosel synth N-acetylhistidine, enzymic oxida-
N,N-distrimethylsilyl (E)-3—tri- from dideox y—D—glucose, 1897 tive coupling to side-chain of N—
butylstannylallylamine, 4121 ,a-dialkyl—, N-protected di- acetyldopamine, 4287
primary —, conversion into phos- peptides containing, 3407 N-aryl— N-carbox y—anhydrides,
phoric acid monoesters by nitro- abs configuration of by modified condn with ester enolates,
sation, 3145 Mosher’s method, 2939 ‘Y-amino-B- etoesters, 3115
proparg ylamines, by copper—cata- aminoacid fluorides, synth, use in N-Boc-statine, synth from N—
lysed aminolysis of bromo-al- peptide synth, 1303 Boc-leucinal, 6783
lenes, 7471
B—aminopropionic acid, Eschweil- N-methyl-, peptide coupling of,
resolution of racemic — by distilla-
1967
tion from chiral acid, 7325 er—Clarke methylation, B-trime-
N-methylation during hydrogeno-
secondary — Ol—alkylation, via oxa- thylammonio—betaine, 3847
lytic deprotection in methanol—
B-arylthiovinyl-, B-alkylthiovi-
zolidines from ydroxyalkyl acetic acid, 7463
t—amine N—oxides, 1443 nyl—glycines, synth, 4717 N-protection using azidomethylox-
chiral synth 2—amino—6—hy-
secondary, enhancing displacement ybenzyloxycarbonyl group, 351
rates by azide, 663 drox y—4—meth yl-8—oxodecanoic non—proteinogenic — with three
secondary, via alkylation of N—-i- acid, leucinostatine constituent,
chiral centres, 2679
err ee. 3985
O-phosphoryl—tyrosine, —threo-
chiral synth on 1,2;5,6—di—O-—iso-
nine, —serine, 1347
tertiary —, oxidation and acylation propylidene (—p—glu-
O-phosphoserine, improved pro-
by TFAA, P-sriftooroacetyi en- cos—3—ulose template, 5801
tection for solid—phase synth,
amines, 5081
cyclodehydration of to pac- 7083
tertiary —, synth from 1—benzotria-
tams by MsCl/NaHCOs, 2299 phosphonomethylphenylalanine,
zolyl Mannich bases using
cysteine to cystine oxidation in incorporation into polypeptides
iCl3/AValkyl or ally! halide,
peptides by DMSO-TFA, 1223 as phosphotyrosyl] analogs, 6061
4247
D-isoglutamine, chemoenzymatic pipecolic acid enantiomers, con-
tritylated bromoalkyl-, synth of
synth, 3529 version into protected 2—amino-
eee and poly—N-ligands,
l enantiosel synth of — via methylpiperidines, 7183
trans—2,5—disubst imidazoli- S—glycosylation of Fmoc-cysteine,
din—2-ones, 1971 —homocysteine, O— of Fmoc—
ethylene glycol cross—linked serine, —threonine, 7613
Aminium salts serine O-sulfate, macrolide com-
Ql—aminoacid, 1283
electron-transfer from hindered ponent from tunicate, 797
olefins to Ar3N*, 117 glycine residues, Ol—subst, by
serine, tyrosine, O—-phosphoryl-,
— with phenyldiazomethane, Pb(OAc),4 oxidn of serine, threo-
incorporation into peptides, 5389
nine moieties, 3163
statine, 4—epi-statine, synth by
histidine, cleavage of imidazole
radical cyclization, 401
ring to asparagine residues by
stereosel synth dolaisoleuine, dola-
Ru(VIII), 5615
Amino acids proine, dolaphenine, dolastatin
histidine, protection and incorpora-
(+)-2-fluoromethyl, —difluorome- tion in solid—phase peptide constituents, 931
thyl tyrosine derivs, 887 synth, 475 synth cis— and trans—pyrroli-
dine—2,4—dicarboxylic acids,
(+)-2-piperazinecarboxylic acid, homocysteine, S—phenyl-—, synth
synth from 4—piperidone, 2469 protected, 4717 analytical resolution, 3049
(—)}-D-t5—hdihr yedroox— y4-.—,va - hydrolytic fragments of calyculin, threonine, D- and L—allo-, and tri-
line, synth from D-ribonolac- 2—methyl—4—aminobutanoic, tiated, from serine, 1031
tone, 1979 2,3—dih ydroxy—4—dimyeltamhi - topographically constrained -, te-
(2S,3R)-2—carboxy—3-pyrrolidi- no—5—methox ypentanoi c acids, trahydroisoquinoline—3—carbox-
neacetic acid, diastereosel synth, cd, abs stereochem, 5605 ylic acid isomers, 5769
3057 hydroxy-, N—Fmoc—O-trityl pro- trans—L—4—hydrox yproline, synth
(E)-S—amino—6—phenyl- tection and use in solid-phase acromelic acid congeners from,
hex—3-enoic acid, synth, 4969 peptide synth, 471 2625