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Synthesis 2008(23): 3864-3868  
DOI: 10.1055/s-0028-1083229
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Intermolecular Stetter Reactions of Aromatic Heterocyclic Aldehydes­ with Arylidenemalonates

Dieter Enders*, Jianwei Han
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
Fax: +49(241)8092127; e-Mail: enders@rwth-aachen.de;
Further Information

Publication History

Received 21 August 2008
Publication Date:
14 November 2008 (online)

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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

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