Enantioselective Organocatalyzed Oxa‐Michael–Aldol Cascade Reactions: Construction of Chiral 4H‐Chromenes with a Trifluoromethylated Tetrasubstituted Carbon …
J Zhang, MJ Ajitha, L He, K Liu, B Dai… - … Synthesis & Catalysis, 2015 - Wiley Online Library
Advanced Synthesis & Catalysis, 2015•Wiley Online Library
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.
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.
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.
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