Synergistic Cu–amine catalysis for the enantioselective synthesis of chiral cyclohexenones?

Chemical Communications Pub Date: 2015-05-01 DOI: 10.1039/C5CC02987B

Abstract

An unprecedented utilization of 1,3-acetonedicarboxylic acid as a 1,3-bis-pro-nucleophile and a reactive acetone surrogate in enantioselective catalysis has been reported. By synergistically activating the ketodiacid by copper catalysis and an α,β-unsaturated aldehyde by amine catalysis, an efficient domino di-decarboxylative Michael/aldol/dehydration sequence takes place leading to valuable chiral cyclohexenones in one single operation in 94 to 99% ee.

Graphical abstract: Synergistic Cu–amine catalysis for the enantioselective synthesis of chiral cyclohexenones
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