Issue 25, 2015

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

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

Supplementary files

Article information

Article type
Paper
Submitted
01 May 2015
Accepted
15 May 2015
First published
15 May 2015

Org. Biomol. Chem., 2015,13, 7076-7083

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

U. Nath, A. Banerjee, B. Ghosh and S. C. Pan, Org. Biomol. Chem., 2015, 13, 7076 DOI: 10.1039/C5OB00878F

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