Asymmetric Organocatalytic Michael Addition–Cyclisation Cascade of Cyclopentane-1,2-dione with Alkylidene Malononitriles

Abstract

An asymmetric organocatalytic cascade reaction between cyclopentane-1,2-diones and alkylidene malononitriles affords highly substituted 4H-pyrans in moderate to high enantiomeric excess. The selective reduction of a bridged double bond leads to the formation of cis-substituted cyclopentanone with three contiguous stereogenic centres.

Key words

organocatalysis - asymmetric catalysis - diketone - pyran - cascade reaction

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• 1 Present affiliation: Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 0B8, Canada

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