Asymmetric Intermolecular Stetter Reactions of Aromatic Heterocyclic Aldehydes with Arylidenemalonates

The asymmetric Michael addition of aromatic heterocyclic aldehydes to arylidenemalonates catalyzed by N-heterocyclic carbenes is described. The ketomalonates are obtained in 84-98% yields and moderate to good enantioselectivities (30-78% ee). The enantiomeric excesses Could be improved to excel lent...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 23; pp. 3864 - 3868
Main Authors Enders, Dieter, Han, Jianwei
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.12.2008
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
N-heterocyclic carbene
organocatalysis
CATALYSIS
Stetter reaction
CARBENES
STRATEGY
umpolung
REACTIVITY
nucleophilic acylation
ACTIVATED DOUBLE-BONDS
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Summary:The asymmetric Michael addition of aromatic heterocyclic aldehydes to arylidenemalonates catalyzed by N-heterocyclic carbenes is described. The ketomalonates are obtained in 84-98% yields and moderate to good enantioselectivities (30-78% ee). The enantiomeric excesses Could be improved to excel lent levels of Lip to 99% ee after a single recrystallization.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0028-1083229