Stereoselective Organocatalysis: Bond Formation Methodologies and Activation Modes

674 Pages·2013·26.07 MB·English

by  Ramon Rios Torres

STEREOSELECTIVE
ORGANOCATALYSIS

STEREOSELECTIVE
ORGANOCATALYSIS
Bond Formation Methodologies
and Activation Modes
Edited by
RAMON RIOS TORRES
University of Southampton
Southampton, United Kingdom
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LibraryofCongressCataloging-in-PublicationData:
Stereoselectiveorganocatalysis:bondformationmethodologiesandactivationmodes/editedby
RamonRiosTorres,UniversityofSouthampton,Southampton,UnitedKingdom.
pagescm
Includesbibliographicalreferencesandindex.
ISBN978-1-118-20353-8(hardback)
1. Catalysis. 2. Chemistry,Organic. 3. Stereochemistry. I. RiosTorres, Ramon,
editorofcompilation.
QD505.S742013
5470.215–dc23
2012050059
PrintedintheUnitedStatesofAmerica
10 9 8 7 6 5 4 3 2 1
CONTENTS
PREFACE vii
CONTRIBUTORS ix
1. INTRODUCTION:AHISTORICALPOINTOFVIEW 1
RamonRiosandXavierCompanyo(cid:1)
2. ACTIVATIONMODESINASYMMETRICORGANOCATALYSIS 11
AlbertMoyano
3. C–CBONDFORMATIONBYALDOLREACTION 81
DorotaGrykoandDominikaWalaszek
4. EXAMPLESOFMETAL-FREEDIRECTCATALYTIC
ASYMMETRICMANNICH-TYPEREACTIONSUSING
AMINOCATALYSIS 129
ArmandoCo(cid:1)rdova
5. C–CBONDFORMATIONBYMICHAELREACTION 147
YongZhangandWeiWang
6. C–CBONDFORMATIONBYDIELS–ALDERANDOTHER
PERICYCLICREACTIONS 205
JohanFranze(cid:1)n
v
vi
CONTENTS
7. N-HETEROCYCLICCARBENE-CATALYZED
C–CBONDFORMATION 231
Xiang-YuChenandSongYe
8. a-ALKYLATIONOFCARBONYLCOMPOUNDS 267
MarekRemes9 andJanVesely(cid:1)
9. OTHERREACTIONSFORC–CBONDFORMATION 313
Yi-XiaJiaandTiexinZhang
10. CASCADEREACTIONSFORMINGC–CBONDS 351
RamonRios,JorgeEsteban,andXavierCompanyo(cid:1)
11. ORGANOCATALYTICC–NBONDFORMATION 381
AitorLanda,RosaLo(cid:1)pez,AntoniaMielgo,MikelOiarbide,
andClaudioPalomo
12. C–OBONDFORMATION 433
Jose(cid:1)Alema(cid:1)nandMariolaTortosa
13. CARBON–HALOGENBONDFORMATION 465
StaceyE.Brenner-Moyer
14. C–OTHERATOMBONDFORMATION(S,SE,B) 493
GiorgioDellaSalaandAlessandraLattanzi
15. ENANTIOSELECTIVEORGANOCATALYTICREDUCTIONS 529
MaurizioBenaglia,MartinaBonsignore,andAndreaGenoni
16. CASCADEREACTIONSFORMINGBOTHC–CBOND
ANDC–HETEROATOMBOND 559
DamienBonne,ThierryConstantieux,YoannCoquerel,
andJeanRodriguez
17. ORGANOCATALYSISINTHESYNTHESISOF
NATURALPRODUCTS 587
YongchengYingandXuefengJiang
INDEX 629
PREFACE
Imagination ismore important than knowledge.
—Albert Einstein
This book is intended to provide an overview of organocatalysis from its
“renaissance” in 2000 until now, and it focuses on the nature of the bond built
rather than on the mode of activation.
Thechaptersincludedinthepresentbookdealwiththenatureofthebondformed
byorganocatalyticmethodologies,rangingfromC–CtoC–heteroatom,andfromthe
original aldol reaction to the highly enantioselective organocascades that improve
reaction outcomes.
Itwasapleasuretobetheeditorofthiscompendium,sinceitprovidedmewith
the opportunity to survey the field of organocatalysis and to honor the work of so
many fine chemists.
I would like to thank all the distinguished scientists and their co-authors for
their rewarding and timely contributions. I acknowledge the great work done by
the Wiley editorial staff—in particular that of Jonathan Rose, whose help was
invaluable.
I also want to thank Professors G. C. Fu, P. Walsh, B. List, and A. Cord(cid:1)ova,
whointroducedmetotheworldofchemistry.Particularly,Iwanttoexpressmydeep
gratitudetoProfessors ListandCord(cid:1)ova,whogavemetheopportunitytostartmy
workinorganocatalysis.Theyintroducemetothatworldandguidedmyfirststeps;
thankstothemIpickedupnotonlyknowledgeaboutorganocatalysisbutalsotheir
love for it.
vii
viii
PREFACE
Finally,Iwanttothankmyparentsforalltheirsupportandhelp.WithoutthemI
could never have carried out this project.
RAMON RIOS TORRES
Southampton
January 2013
CONTRIBUTORS
JOSE´ ALEMA´N, DepartamentodeQuimicaOrganica(C-I),UniversidadAutonomade
Madrid, Cantoblanco, 28049 Madrid, Spain
MAURIZIO BENAGLIA, Dipartimento di Chimica Organica e Industriale, Universita
degli Studi di Milano, 20133 Milano, Italy
DAMIEN BONNE, Aix-Marseille Universite, iSm2, UMR CNRS 6263, Centre St.
Jerome, service 531, 13397 Marseille Cedex 20, France
MARTINABONSIGNORE, DipartimentodiChimicaOrganicaeIndustriale,Universita
degli Studi di Milano, 20133 Milano, Italy
STACEY E. BRENNER-MOYER, Department of Chemistry, Brooklyn College and the
CityUniversityofNewYork,2900BedfordAvenue,Brooklyn,NewYork11210,
United States
XIANG-YU CHEN, Institute of Chemsitry, CAS, Beijing, 100190, China
XAVIER COMPANY(cid:1)o, Universitat de Barcelona, Mart(cid:1)ı i Franqu(cid:3)es 1-11, Barcelona
08028, Spain
THIERRYCONSTANTIEUX, Aix-MarseilleUniversite,iSm2,UMRCNRS6263,Centre
St. Jerome, service 531, 13397 Marseille Cedex 20, France
YOANN COQUEREL, Aix-Marseille Universite, iSm2, UMR CNRS 6263, Centre
St. Jerome, service 531, 13397 Marseille Cedex 20, France
ARMANDOC(cid:1)oRDOVA, DepartmentofOrganicChemistry,TheArrheniusLaboratory,
Stockholm University, 106 91 Stockholm, Sweden; and Department of Natural
ix
x
CONTRIBUTORS
Sciences, Engineering and Mathematics, Mid Sweden University, SE-851 70
Sundsvall, Sweden
GIORGIO DELLA SALA, Dipartimento di Chimica, Universita di Salerno, 84084,
Fisciano, Italy
JORGEESTEBAN, UniversitatdeBarcelona,Mart(cid:1)ıiFranqu(cid:3)es1-11,Barcelona08028,
Spain
JOHAN FRANZE´N, Royal Institute of Technology (KTH), Department of Chemistry,
Organic Chemistry, S-100 44, Stockholm, Sweden
ANDREAGENONI, DipartimentodiChimicaOrganicaeIndustriale,Universitadegli
Studi di Milano, 20133 Milano, Italy
DOROTA GRYKO, Institute of Organic Chemistry, Polish Academy of Sciences,
Kasprzaka 44/52, 01-224 Warsaw, Poland
YI-XIA JIA, College of Chemical Engineering and Materials Science, Zhejiang
University of Technology, Hangzhou, China
XUEFENG JIANG, Shanghai Key Laboratory of Green Chemistry and Chemical
Process, East China Normal University, Shanghai, 200062, People’s Republic
of China
AITOR LANDA, Departamento de Qu(cid:1)ımica Orga´nica I, Facultad de Qu(cid:1)ımica, Uni-
versidad del Pa(cid:1)ıs Vasco, UPV/EHU, Paseo Manuel Lardizabal, 3, 20018, San
Sebastia´n, Spain
ALESSANDRA LATTANZI, Dipartimento di Chimica, Universita di Salerno, 84084,
Fisciano, Italy
ROSA L(cid:1)oPEZ, Departamento de Qu(cid:1)ımica Orga´nica I Facultad de Qu(cid:1)ımica, Uni-
versidad del Pa(cid:1)ıs Vasco, UPV/EHU, 20018, San Sebastia´n, Spain
ANTONIA MIELGO, Departamento de Qu(cid:1)ımica Orga´nica I, Facultad de Qu(cid:1)ımica,
Universidad del Pa(cid:1)ıs Vasco, UPV/EHU, 20018, San Sebastia´n, Spain
ALBERT MOYANO, Universitat de Barcelona, Mart(cid:1)ı i Franqu(cid:3)es 1-11, Barcelona
08028, Spain
MIKEL OIARBIDE, Departamento de Qu(cid:1)ımica Orga´nica I, Facultad de Qu(cid:1)ımica,
Universidad del Pa(cid:1)ıs Vasco, UPV/EHU, 20018, San Sebastia´n, Spain
CLAUDIO PALOMO, Departamento de Qu(cid:1)ımica Orga´nica I, Facultad de Qu(cid:1)ımica,
Universidad del Pa(cid:1)ıs Vasco, UPV/EHU, 20018, San Sebastia´n, Spain
MAREKREME9s, CharlesUniversityinPrague,Hlavova2030,Prague12840,Czech
Republic
RAMONRIOS, UniversityofSouthampton,HighfieldCampus,SO171BJSouthampton,
UnitedKingdom