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Enantioselective Organocatalyzed Oxa‐Michael–Aldol Cascade Reactions: Construction of Chiral 4 H ‐Chromenes with a Trifluoromethylated Tetrasubstituted Carbon Stereocenter
Author(s) -
Zhang Jing,
Ajitha Manjaly J.,
He Lin,
Liu Kai,
Dai Bin,
Huang KuoWei
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400977
Subject(s) - stereocenter , chemistry , enantioselective synthesis , aldol reaction , organocatalysis , iminium , cascade , michael reaction , cascade reaction , organic chemistry , asymmetric carbon , combinatorial chemistry , catalysis , stereochemistry , optically active , chromatography
The first organocatalytic asymmetric synthesis of 4 H ‐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.