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Synthesis 2008(23): 3864-3868
DOI: 10.1055/s-0028-1083229
DOI: 10.1055/s-0028-1083229
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Asymmetric Intermolecular Stetter Reactions of Aromatic Heterocyclic Aldehydes with Arylidenemalonates
Further Information
Publication History
Received
21 August 2008
Publication Date:
14 November 2008 (online)


Abstract
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 excellent levels of up to 99% ee after a single recrystallization.
Key words
Stetter reaction - N-heterocyclic carbene - organocatalysis - nucleophilic acylation - umpolung