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Asymmetric Michael Addition/Intramolecular Cyclization Catalyzed by Bifunctional Tertiary Amine–Squaramides: Construction of Chiral 2‐Amino‐4 H ‐chromene‐3‐Carbonitrile Derivatives
Author(s) -
Gao Yu,
Du DaMing
Publication year - 2014
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201402567
Subject(s) - squaramide , bifunctional , malononitrile , michael reaction , intramolecular force , catalysis , chemistry , amine gas treating , tertiary amine , enantioselective synthesis , organic chemistry , organocatalysis , medicinal chemistry
Abstract The efficient asymmetric Michael addition/intramolecular cyclization of malononitrile with dienones catalyzed by a chiral bifunctional tertiary amine–squaramide catalyst for the synthesis of chiral 2‐amino‐4 H ‐chromene‐3‐carbonitrile derivatives was developed. The corresponding products were obtained in good to excellent yields (up to 99 %) with excellent enantioselectivities (up to 98 % ee ) for most of the bisarylidenecyclopentanones.