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Enantioselective Aza‐Henry Reaction of Imines Bearing a Benzothiazole Moiety Catalyzed by a Cinchona ‐Based Squaramide
Author(s) -
He HaiXiao,
Yang Wen,
Du DaMing
Publication year - 2013
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.201200957
Subject(s) - chemistry , squaramide , enantioselective synthesis , moiety , benzothiazole , nitromethane , nitroaldol reaction , cinchona , catalysis , organic chemistry , organocatalysis , medicinal chemistry , combinatorial chemistry
An efficient enantioselective aza‐Henry reaction of nitroalkanes to imines bearing a benzothiazole moiety catalyzed by a Cinchona ‐based squaramide has been developed. In the reaction of imines, the corresponding products were obtained in good to excellent yields (up to 99%) with excellent enantioselectivities (up to >99% ee ) for most of the aromatic substituted imines. The imines with electron‐withdrawing groups gave better yields than those bearing electron‐donating groups in the aza‐Henry reaction. Moreover, a one‐pot three‐component enantioselective aza‐Henry reaction using 2‐aminobenzothiazoles, aldehydes, and nitromethane was also developed. Moderate to good yields and high enantioselectivities were obtained in the one‐pot cases (up to 98% ee ).