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Enantioselective Organocatalyzed Oxa-Michael-Aldol Cascade Reactions: Construction of Chiral 4H-Chromenes with a Trifluoromethylated Tetrasubstituted Carbon Stereocenter
Journal article   Peer reviewed

Enantioselective Organocatalyzed Oxa-Michael-Aldol Cascade Reactions: Construction of Chiral 4H-Chromenes with a Trifluoromethylated Tetrasubstituted Carbon Stereocenter

Jing Zhang, Manjaly J. Ajitha, Lin He, Kai Liu, Bin Dai and Kuo-Wei Huang
Advanced synthesis & catalysis, Vol.357(5), pp.967-973
23/03/2015

Abstract

Chemistry Chemistry, Applied Chemistry, Organic Physical Sciences Science & Technology
The first organocatalytic asymmetric synthesis of 4H-chromenes bearing a trifluoromethylated tetrasubstituted carbon center is presented. Chiral secondary amines promote the oxa-Michaelaldol cascade reaction between alkynals and 2-trifluoroacetylphenols via iminium-allenamine activation to produce pharmaceutically important heterocycles with excellent enantioselectivities. The proposed reaction can be scaled-up easily with maintenance of the excellent enantioselectivity.

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