Chiral Reagents for Asymmetric Synthesis [Handbook of Reagents for Organic Synthesis]

665 Pages·2003·15.189 MB·English

by  L. Paquette

Handbook of Reagents
for Organic Synthesis
Chiral Reagents for
Asymmetric Synthesis
Edited by
Leo A. Paquette
The Ohio State University, Columbus, OH, USA
Copyright © 2003 John Wiley & Sons Ltd,
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Library of Congress Cataloguing-in-Publication Data
Handbook of reagents for organic synthesis,
p. cm.
Includes bibliographical references.
Contents: [1] Reagents, auxiliaries, and catalysts for C-C bond
formation / edited by Robert M. Coates and Scott E. Denmark
[2] Oxidising and reducing agents / edited by Steven D. Burke and
Riek L. Danheiser [3] Acidic and basic reagents / edited by
Hans J. Reich and James H. Rigby [4] Activating agents and
protecting groups / edited by Anthony J. Pearson and William R. Roush
[5] Chiral Reagents for Asymmetric Synthesis / edited by Leo A. Paquette
ISBN 0-471-97924-4 (v. 1). ISBN 0-471-97926-0 (v. 2)
ISBN 0-471-97925-2 (v. 3) ISBN 0-471-97927-9 (v. 4)
ISBN 0-470-85625-4 (v. 5)
1. Chemical tests and reagents. 2. Organic compounds-Synthesis.
QD77.H37 1999
547'.2 dc 21 98-53088
CIP
British Library Cataloguing in Publication Data
A catalogue record for this book is available from the British Library
ISBN 0 470 85625 4
Typeset in 9^/1 \\ pt Times Roman by Thomson Press (India) Ltd., New Delhi
Printed and bound in Great Britain by Antony Rowe, Chippenham, Wiltshire
This book is printed on acid-free paper responsibly manufactured from sustainable forestry
in which at least two trees are planted for each one used for paper production.
e-EROS Editorial Board
Editor-in-Chief
Leo A. Paquette
The Ohio State University, Columbus, OH, USA
Executive Editors
David Crich
University of Illinois, Chicago, IL, USA
Philip L. Fuchs
Purdue University, West Lafayette, IN, USA
Peter Wipf
University of Pittsburgh, Pittsburgh, PA, USA
st
EROS 1 Print Edition Editorial Board
Editor-in-Chief
Leo A. Paquette
The Ohio State University, Columbus, OH, USA
Editors
Steven D. Burke Robert M. Coates Rick L. Danheiser
University of Wisconsin University of Illinois Massachusetts Institute of
at Madison, at Urbana-Champaign, Technology, Cambridge,
WI, USA IL, USA MA, USA
Scott E. Denmark David J. Hart Lanny S. Liebeskind
University of Illinois The Ohio State University, Emory University, Atlanta,
at Urbana-Champaign, Columbus, OH, USA GA, USA
IL, USA
Dennis C. Liotta Anthony J. Pearson Hans J. Reich
Emory University, Atlanta, Case Western Reserve University, University of Wisconsin at Madison,
CA, USA Cleveland, OH, USA WI, USA
James H. Rigby William R. Roush
Wayne State University, Detroit, Indiana University, Bloomington,
MI, USA IN, USA
Assistant Editors
James P. Edwards Mark Volmer
Ligand Pharmaceuticals, San Diego, Emory University, Atlanta,
CA, USA GA, USA
International Advisory Board
Leon A. Ghosez Jean-Marie Lehn Steven V. Ley
Universite Catholique Universite Louis Pasteur, University of Cambridge,
de Louvain, Belgium Strasbourg, France UK
Chun-Chen Liao • XT ** J r*- - -KK A
T
. j . „ Lewis N. Mander Giorgio Modena
N . . T TT - i ^ . Australian National University, Universitd di Padua,
UTTniversity, Hsinchu, Taiwan ^i A i- r i
J Canberra, Australia Italy
Ryoji Noyori
Nagoya University, Japan Gerald Pattenden Edward Piers
University of Nottingham, University of British Columbia,
Pierre Potier UK Vancouver, Canada
CNRS, Gif-sur-Yvette, France
W. Nico Speckamp Ekkehard Winterfeldt
Hishashi Yamomoto Universiteit van Amsterdam, Universitdt Hannover,
Nagoya University, Japan The Netherlands Germany
Preface
As stated in its Preface, the major motivation for our edited by Robert M. Coates and Scott E. Denmark
undertaking publication of the Encyclopedia of Reagents for
Oxidizing and Reducing Agents
Organic Synthesis was "to incorporate into a single work a
edited by Steven D. Burke and Rick L. Danheiser
genuinely authoritative and systematic description of the
utility of all reagents used in organic chemistry." By all Acidic and Basic Reagents
accounts, this reference compendium succeeded admirably edited by Hans J. Reich and James H. Rigby
in approaching this objective. Experts from around the
Activating Agents and Protecting Groups
globe contributed many relevant facts that define the various
edited by Anthony J. Pearson and William R. Roush
uses characteristic of each reagent. The choice of a masthead
format for providing relevant information about each entry, Each of the volumes contains a selected compilation of those
the highlighting of key transformations with illustrative entries from the original Encyclopedia that bear on the specific
equations, and the incorporation of detailed indexes topic. Ample listings can be found to functionally related
serve in tandem to facilitate the retrieval of desired reagents contained in the original work. For the sake of current
information. awareness, references to recent reviews and monographs have
Notwithstanding these accomplishments, the editors came oeen included, as have relevant new procedures from Organic
to recognize that the large size of this eight-volume work and Syntheses.
its cost of purchase often deterred the placement of copies of The present volume entitled Chiral Reagents for Asym-
the Encyclopedia in or near laboratories where the need for this metric Synthesis constitutes the fifth entry into a continuing
type of information is most critical. In an effort to meet this series of utilitarian reference works. As with its predecessors,
demand in a cost-effective manner, the decision was made to :his handbook is intended to be an affordable, enlightening
cull from the major work that information having the highest :ompilation that will hopefully find its way into the labora-
probability for repeated consultation and to incorporate the :ories of all practicing synthetic chemists. Every attempt has
same into a set of handbooks. The latter would also be Deen made to be of the broadest possible relevance and the
purchasable on a single unit basis. expectation is that my colleagues will share in this opinion.
The ultimate result of these deliberations was the
publication of the Handbook of Reagents for Organic Leo A. Paquette
Synthesis, the first four volumes of which appeared in 1999: Department of Chemistry
Reagents, Auxiliaries, and Catalysts for C-C Bond The Ohio State University
Formation Columbus, OH, USA
Introduction
All of us are aware of the sharp increase in demand for subjects related to this general theme. Following that, there is a
enantiomerically pure reagents and products that has tran- section that illustrates those procedures appearing in volumes
spired over the past twenty-five years or so. To some extent, the 68-78 of Organic Syntheses that feature the detailed pre-
move in this direction has been brought on by the quest by paration of enantiomerically enriched end-products. The
synthetic organic chemists for optically pure natural product overall intent is to assemble in manageable format as much
targets and for effective asymmetric catalysts. More signifi- indispensable information dealing with the subject of Chiral
cantly, this activity has been spurred on throughout the world Reagents for Asymmetric Synthesis as possible. To this end, the
by governmental oversight agencies whose responsibility it entries are grouped into the following categories: alcohols,
is to guarantee the availability of pure drugs for human aldehydes, amides and lactams, amino compounds, carbo-
consumption. As a consequence, the international medicinal hydrate derivatives, diols, esters and lactones, heterocycles,
chemistry community continues to upgrade its search for ketones, sulfur compounds, phosphines, and miscellaneous.
economic ways to develop chiral technology. The need for In the majority of cases, asymmetric reactions are involved.
chiral, nonracemic raw materials, intermediates, and bioactive Enantioselective applications of transition metal catalysts can
end products continues to grow at a rapid rate. In the light of be found throughout the volume. In the body of the text, no
these developments, this seemed an appropriate time for attempt has been made to group the reagents in other than
assembly into a single volume of a compilation listing many of alphabetical order. The benefit derived from scanning its pages
the optically active reagents and catalysts in use at the present is thereby maximized.
time. Finally, we hope that the reader will find this volume to
The selection covered in this volume comes from two constitute the useful and convenient handbook it was designed
sources. The first is the Encyclopedia of Reagents for Organic to be. This goal will have been reached if the present com-
Synthesis (EROS) which was published in 1995. In the pilation develops into a valued adjunct to mainstream synthetic
intervening time, new entries have been written by many practice.
experts in the field for incorporation into the ever-expanding
electronic version of the same work (e-EROS). As to be
expected, the compilation includes both well recognized and Leo A. Paquette
lesser known reagents and ligands. In order to assist the re- Department of Chemistry
searcher searching for relevant information, this Introduction The Ohio State University
is followed by a listing of Recent Reviews and Monographs on Columbus, OH, USA
General Abbreviations
Ac acetyl DIEA = DIPEA
acac acetylacetonate DIOP 2,3-6Msopropylidene-2,3-dihydroxy-1,4-bis-
AIBN 2,2/-azobisisobutyronitrile (diphenylphosphino)butane
Ar aryl DIPEA diisopropylethylamine
diphos =dppe
BBN borabicyclo[3.3.1]nonane DIPT diisopropyl tartrate
BCME dis(chloromethyl)ether DMA dimethylacetamide
BHT butylated hydroxytoluene (2,6-di-f-butyl-/?- DMAD dimethyl acetylenedicarboxylate
cresol) DMAP 4-(dimethylamino)pyridine
BINAL-H 2,2'-dihydroxy-1, l'-binaphthyl-lithium DME 1,2-dimethoxyethane
aluminum hydride DMF dimethylformamide
BINAP 2,2'-bis(diphenylphosphino)-1,1 '-binaphthyl dmg dimethylglyoximato
BINOL l,l'-bi-2,2'-naphthol DMPU A^Af'-dimethylpropyleneurea
bipy 2,2/-bipyridyl DMS dimethyl sulfide
BMS borane-dimethyl sulflde DMSO dimethyl sulfoxide
Bn benzyl DMTSF dimethyl(methylthio) sulfonium
B oc ^-butoxycarbonyl tetrafluoroborate
BOM benzyloxymethyl dppb 1,4-bis(diphenylphosphino)butane
bp boiling point dppe 1,2-bis(diphenylphosphino)ethane
Bs brosyl (4-bromobenzenesulfonyl) dppf 1,1 /-bis(diphenylphosphino)ferrocene
BSA N, O-bis(trimethylsilyl)acetamide dppp 1,3-bis(diphenylphosphino)propane
Bu rc-butyl DTBP di-f-butyl peroxide
Bz benzoyl
EDA ethyl diazoacetate
CAN cerium(IV) ammonium nitrate EDC 1 -ethyl-3-(3-dimethylaminopropyl)-
Cbz benzyloxycarbonyl carbodiimide
CDI A^W-carbonyldiimidazole EDCI =EDC
CHIRAPHOS 2,3-bis(diphenylphosphino)butane ee enantiomeric excess
Chx - Cy EE 1-ethoxyethyl
cod cyclooctadiene Et ethyl
cot cyclooctatetraene ETSA ethyl trimethylsilylacetate
Cp cyclopentadienyl EWG electron withdrawing group
CRA complex reducing agent
CSA 10-camphorsulfonic acid Fc ferrocenyl
CSI chlorosulfonyl isocyanate Fmoc 9-fluorenylmethoxycarbonyl
Cy cyclohexyl fp flash point
d density Hex n-hexyl
DABCO 1,4-diazabicyclo[2.2.2]octane HMDS hexamethyldisilazane
DAST MN'-diethylaminosulfur trifluoride HMPA hexamethylphosphoric triamide
dba dibenzylideneacetone HOBt 1-hydroxybenzotriazole
DBAD di-f-butyl azodicarboxylate HOBT =HOBt
DBN l,5-diazabicyclo[4.3.0]non-5-ene HOSu jV-hydroxysuccinimide
DBU l,8-diazabicyclo[5.4.0]undec-7-ene
DCC A^A^-dicyclohexylcarbodiimide Im imidazole (imidazolyl)
DCME dichloromethyl methyl ether Ipc isopinocampheyl
DDO dimethyldioxirane IR infrared
DDQ 2,3-dichloro-5,6-dicyano-1,4-benzoquinone
de diastereomeric excess KHDMS potassium hexamethyldisilazide
DEAD diethyl azodicarboxylate
DET diethyl tartrate LAH lithium aluminum hydride
DIBAL diisobutylaluminum hydride LD dose that is lethal to 50% of test subjects
50
LDA lithium diisopropylamide PMDTA AWA^A^'-pentamethyldiethylene-
LDMAN lithium l-(dimethylamino)naphthalenide triamine
LHMDS = LiHMDS PPA polyphosphoric acid
LICA lithium isopropylcyclohexylamide PPE polyphosphate ester
LiHMDS lithium hexamethyldisilazide PPTS pyridinium /7-toluenesulfonate
LiTMP lithium 2,2,6,6-tetramethylpiperidide Pr rc-propyl
LTMP = LiTMP PTC phase transfer catalyst/catalysis
LTA lead tetraacetate PTSA p-toluenesulfonic acid
lut lutidine py pyridine
RAMP (R)-1 -amino-2-(methoxymethyl)pyrrolidine
ra-CPBA ra-chloroperbenzoic acid
rt room temperature
MA maleic anhydride
MAD methylaluminum bis(2,6-di-£-butyl-4-
salen bis(salicylidene)ethylenediamine
methylphenoxide)
SAMP (S)-1 -amino-2-(methoxymethyl)pyrrolidine
MAT methylaluminum bis(2,4,6-tri-£-
SET single electron transfer
butylphenoxide)
Sia siamyl (3-methyl-2-butyl)
Me methyl
MEK methyl ethyl ketone TASF tris(diethylamino)sulfonium
MEM (2-methoxyethoxy)methyl difluorotrimethylsilicate
MIC methyl isocyanate TBAB tetrabutylammonium bromide
MMPP magnesium monoperoxyphthalate TBAF tetrabutylammonium fluoride
MOM methoxymethyl TBAD = DBAD
MoOPH oxodiperoxomolybdenum(pyridine)- TBAI tetrabutylammonium iodide
(hexamethylphosphoric triamide) TBAP tetrabutylammonium perruthenate
mp melting point TBDMS /-butyldimethylsilyl
MPM =PMB TBDPS f-butyldiphenylsilyl
Ms mesyl (methanesulfonyl) TBHP r-butyl hydroperoxide
MS mass spectrometry; molecular sieves TBS = TBDMS
MTBE methyl J-butyl ether TCNE tetracyanoethylene
MTM methylthiomethyl TCNQ 7,7,8,8-tetracyanoquinodimethane
MVK methyl vinyl ketone TEA triethylamine
TEBA triethylbenzylammonium chloride
n refractive index TEBAC =TEBA
NaHDMS sodium hexamethyldisilazide TEMPO 2,2,6,6-tetramethylpiperidinoxyl
Naph naphthyl TES triethylsilyl
NBA Af-bromoacetamide Tf triflyl (trifluoromethanesulfonyl)
nbd norbornadiene (bicyclo[2.2.1]hepta- TFA trifluoroacetic acid
2,5-diene) TFAA trifluoroacetic anhydride
NBS N-bromosuccinimide THF tetrahydrofuran
NCS A^-chlorosuccinimide THP tetrahydropyran; tetrahydropyranyl
NIS A^-iodosuccinimide Thx thexyl (2,3-dimethyl-2-butyl)
NMO A^-methylmorpholine Af-oxide TIPS triisopropylsilyl
NMP Af-methyl-2-pyrrolidinone TMANO trimethylamine N-oxide
NMR nuclear magnetic resonance TMEDA ^,^,^,^-tetramethylethylenediamine
NORPHOS bis(diphenylphosphino)bicyclo[2.2.1]-hept- TMG 1,1,33-tetramethylguanidine
5-ene TMS trimethylsilyl
Np =Naph ToI p-tolyl
TPAP tetrapropylammonium perruthenate
PCC pyridinium chlorochromate TBHP f-butyl hydroperoxide
PDC pyridinium dichromate TPP tetraphenylporphyrin
Pent ft-pentyl Tr trityl (triphenylmethyl)
Ph phenyl Ts tosyl (p-toluenesulfonyl)
phen 1,10-phenanthroline TTN thallium(III) nitrate
Phth phthaloyl
UHP urea-hydrogen peroxide complex
Piv pivaloyl
PMB /?-methoxybenzyl
Z =Cbz
Contents
Preface .................................................................................................................................... xi
Introduction .............................................................................................................................. xiii
General Abbreviations ............................................................................................................. xv
1. Recent Review Articles and Monographs .................................................................... 1
2. Organic Synthesis Procedures Featuring Chiral, Non-racemic Reagent
Preparation, Volumes 68-78 ........................................................................................... 7
3. (S)-Aceto(carbonyl)(cyclopentadienyl)-(triphenylphosphine)iron to
2-Azabicyclo[2.2.1]hept-5-en-3-one ............................................................................... 21
3.1 (S)-Aceto(carbonyl)(cyclopentadienyl)-(triphenylphosphine)iron ....................................... 21
3.2 Allylcyclopentadienyl[(4R,trans)- and (4S,trans)-α,α,α’,α’-tetraphenyl-1,3-dioxolane-
4,5-dimethanolato-O,O’]titanium [Cp(R,R)-Ti[All] and Cp(S,S)-Ti[All]] ............................... 23
3.3 B-Allyldiisocaranylborane ................................................................................................... 26
3.4 (1R,2S)-1-Amino-2,3-dihydro-1H-inden-2-ol ....................................................................... 27
3.5 (S)-1-Amino-2-hydroxymethylindoline ................................................................................ 30
3.6 (S)-1-Amino-2-methoxymethylpyrrolidine ........................................................................... 32
3.7 2-Amino-3-methyl-1,1-diphenyl-1-butanol .......................................................................... 36
3.8 3-Amino-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol ............................................................... 38
3.9 (S)-4-Anilino-3-methylamino-1-butanol ............................................................................... 40
3.10 (S)-2-(Anilinomethyl)pyrrolidine .......................................................................................... 41
3.11 L-Aspartic Acid .................................................................................................................... 42
3.12 2-Azabicyclo[2.2.1]hept-5-en-3-one .................................................................................... 44
4. Baker’s Yeast to (R)-(+)-t-Butyl 2-(p-Tolylsulfinyl)propionate .................................... 45
4.1 Baker’s Yeast ...................................................................................................................... 45
4.2 (1R,5R)-2H-1,5-Benzodithiepin-3(4H)-one 1,5-Dioxide ...................................................... 48
4.3 1-Benzoyl-2-t-butyl-3,5-dimethyl-4-imidazolidinone ............................................................ 50
4.4 (2S,4S)-3-Benzoyl-2-t-butyl-4-methyl-1,3-oxazolidin-5-one ............................................... 51
4.5 1-Benzoyl-2(S)-tert-butyl-3-methylperhydropyrimidin-4-one ............................................... 53
4.6 Benzyl(methoxymethyl)methylamine .................................................................................. 56
4.7 (S)-4-Benzyl-2-oxazolidinone ............................................................................................. 57
4.8 N-Benzyloxycarbonyl-L-serine β-Lactone ........................................................................... 68
vii
viii Contents
4.9 2-[2-[(Benzyloxy)ethyl]-6,6-dimethylbicyclo[3.3.1]-3-nonyl]-9-borabicyclo[3.3.1]nonane .... 70
4.10 (R,R)-1-(2’-Benzyloxymethylphenyl)-2,5-dimethylphospholane ......................................... 71
4.11 N-Benzylquininium Chloride ............................................................................................... 72
4.12 (S)-4-Benzyl-2,2,5,5-tetramethyloxazolidine ....................................................................... 73
4.13 (Bicyclo[2.2.1]hepta-2,5-diene)[(2S,3S)-bis(diphenylphosphino)butane]rhodium
Perchlorate ......................................................................................................................... 74
4.14 (Bicyclo[2.2.1]hepta-2,5-diene)[1,4-
bis(diphenylphosphino)butane]rhodium(I)Tetrafluoroborate ............................................... 76
4.15 (1R,1’R,2R,2’R)-[1,1’-Bicyclopentyl-2,2’-diylbisdiphenylphosphine] ................................... 81
4.16 1,1’-Binaphthalene-2,2’-dithiol ............................................................................................ 83
4.17 (R)-1,1’-Bi-2,2’-naphthol ..................................................................................................... 86
4.18 (R)-1,1’-Bi-2,2’-naphthotitanium Dichloride ......................................................................... 91
4.19 (R)-1,1’-Bi-2,2’-naphthotitanium Diisopropoxide ................................................................. 94
4.20 (S)-2,2’Binaphthoyl(R,R)-di(1-phenylethyl)aminoylphosphine ........................................... 95
4.21 1,1’-Binaphthyl-2,2’-diyl Hydrogen Phosphate .................................................................... 97
4.22 Bis(α-camphorquinone dioximato)cobalt ............................................................................ 98
4.23 (R,R)-1,2-Bis(aminocarbonylphenyl-2’-diphenylphosphino)cyclohexane ........................... 99
4.24 Bis(bicyclo[2.2.1]hepta-2,5-diene)-rhodium Perchlorate-(R)-1-(S)-1’,2-
Bis(diphenylphosphino)ferrocenylethanol ........................................................................... 104
4.25 (1S,9S)-1,9-Bis{[(t-butyl)dimethylsilyloxy]methyl}-5-cyanosemicorrin ................................ 105
4.26 (R,R)-Bis(tert-butylmethylphosphino)methane ................................................................... 107
4.27 2,2-Bis{[2-[4(S)-tert-butyl-1,3-oxazolinyl]}propane .............................................................. 108
4.28 Bis(cyclohexyl isocyanide)gold(I) Tetrafluoroborate-(R)-N-[2-(N,N-Dimethylamino)ethyl]-
N-methyl-1-(S)-1’,2-bis(diphenylphosphino)ferrocenyl]ethylamine ..................................... 115
4.29 Bis(1,5-cyclooctadiene)rhodium Tetrafluoroborate-(R)-2,2’Bis(diphenylphosphino)-
1,1’-binaphthyl .................................................................................................................... 118
4.30 (S,S)-1,2-Bis(2,5-diethylphospholano)benzene .................................................................. 119
4.31 1,2-Bis((2S,5S)-2,5-dimethylphospholano)benzene (S,S)-Me-DuPhos,
1,2-Bis((2R,5R)2,5-dimethylphospholano)benzene (R,R)-Me-DuPhos .............................. 123
4.32 [Bis(4R,5S)-4,5-diphenyl-1,3-oxazolin-2-yl]methane [Bis(4S,5R)-4,5-diphenyl-1,3-
oxazolin-2-yl]methane ......................................................................................................... 126
4.33 (R)- & (S)-2,2’-Bis(diphenylphosphino)-1,1’-binaphthyl ...................................................... 128
4.34 (2R,3R)-2,3-Bis(diphenylphosphino)butane ....................................................................... 132
4.35 (R)-7,7’-Bis(diphenylphosphinomethyl)-2,2’-dimethoxy-1,1’-binaphthyl ............................. 133
4.36 (η5,η5-1S,2R,4S,5R-1,4-Bis(indenyl)-2,5-diisopropylcyclohexane)titanium Dichloride ....... 134
4.37 2,6-Bis[(4S)-4-isopropyloxazolin-2-yl]pyridine .................................................................... 135
4.38 2,6-Bis[(S)-4’-isopropyloxazolin-2’-yl](pyridine)rhodium Trichloride ................................... 136
4.39 trans-2,5-Bis(methoxymethyl)pyrrolidine ............................................................................ 138
4.40 Bis[(4S)-(1-methylethyl)oxazolin-2-yl]methane ................................................................... 140
4.41 (R)-3,3’-Bis(triphenylsilyl)binaphthomethylaluminum .......................................................... 144
4.42 (–)-endo-Bornyltriazolinedione ............................................................................................ 145