Organocatalytic asymmetric Michael addition of 1-acetylcyclohexene and 1-acetylcyclopentene to nitroolefins?

Organic & Biomolecular Chemistry Pub Date: 2015-05-15 DOI: 10.1039/C5OB00878F

Abstract

Enantioselective organocatalytic Michael addition reactions of 1-acetylcyclohexene, 1-acetylcyclopentene and 1-acetylcyclobutene to nitroolefins have been developed. This is the first report where an α-branched enone has been activated by an amine catalyst for the asymmetric Michael addition reaction to an electrophile. The Michael products have also been cyclized to bicyclic compounds.

Graphical abstract: Organocatalytic asymmetric Michael addition of 1-acetylcyclohexene and 1-acetylcyclopentene to nitroolefins
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