Highly Enantioselective Intermolecular Stetter Reaction of Simple Acrylates: Synthesis of a-Chiral ?-Ketoesters

Simple Stetter: A novel N-heterocyclic carbene (NHC) was designed by combining an electron-rich 2,6-dimethoxy substituent and an underestimated yet promising chiral motif. With this NHC in hand, a highly enantioselective intermolecular Stetter reaction of simple acrylates was developed, yielding ver...

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Bibliographic Details
Published inChemistry : a European journal Vol. 18; no. 51; pp. 16297 - 16301
Main Authors Wurz, Nathalie E., Daniliuc, Constantin G., Glorius, Frank
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 14.12.2012
Wiley Subscription Services, Inc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
CATALYSIS
N-HETEROCYCLIC CARBENE
ACID
Stetter reaction
BENZOIN CONDENSATION
acrylates
ALDEHYDES
asymmetric catalysis
CYCLOPROPENES
ENALS
organocatalysis
TRIAZOLIUM SALTS
synthetic methods
HYDROACYLATION
N-heterocyclic carbenes
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Summary:Simple Stetter: A novel N-heterocyclic carbene (NHC) was designed by combining an electron-rich 2,6-dimethoxy substituent and an underestimated yet promising chiral motif. With this NHC in hand, a highly enantioselective intermolecular Stetter reaction of simple acrylates was developed, yielding versatile α-chiral γ-ketoesters. This represents the first catalytic asymmetric route towards these valuable compounds (see scheme).
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 14
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201202432