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Synfacts 2010(8): 0954-0954  
DOI: 10.1055/s-0030-1257807
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Cyclopropanation of α-Substituted α,β-Unsaturated Aldehydes

Contributor(s): Benjamin List, Saihu Liao
V. Terrasson, A. van der Lee, R. M. de Figueiredo*, J. M. Campagne*
Ecole Nationale Supérieure de Chimie and Institut Européen des Membranes, Montpellier, France
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Publication History

Publication Date:
22 July 2010 (online)

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Significance

An efficient enantioselective cyclopropanation of α-substituted α,β-unsaturated ­aldehydes catalyzed by a secondary amine is reported by the authors. In the presence of 20 mol% catalyst 3 and a base additive (three equivalents of 2,6-lutidine or five equivalents of N-methylimidazole), various α-substituted acroleins 1 react with bromomalonate (2) smoothly via a domino Michael­-α-alkylation reaction sequence, furnishing the corresponding cyclopropanes 4 bearing a chiral quaternary center in good yields and high enantiomeric purity (er up to 98.5:1.5).