Enantioselective organocatalyzed Oxa-Michael-Aldol cascade reactions: Construction of chiral 4H-chromenes with a trifluoromethylated tetrasubstituted carbon stereocenter

Jing Zhang, Manjaly John Ajitha, Lin He, Kai Liu, Bin Dai, Kuo-Wei Huang

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

The first organocatalytic asymmetric synthesis of 4H-chromenes bearing a trifluoromethylated tetrasubstituted carbon center is presented. Chiral secondary amines promote the oxa-Michael-aldol 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. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Original languageEnglish (US)
Pages (from-to)967-973
Number of pages7
JournalAdvanced Synthesis & Catalysis
Volume357
Issue number5
DOIs
StatePublished - Mar 13 2015

ASJC Scopus subject areas

  • Organic Chemistry
  • Catalysis

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