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Highly Enantioselective Biginelli Reaction Catalyzed by Double Axially Chiral Bisphosphorylimides
Author(s) -
An Dong,
Fan YanSen,
Gao Yang,
Zhu ZiQian,
Zheng LiangYu,
Zhang SuoQin
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301560
Subject(s) - chemistry , enantioselective synthesis , thiourea , ethyl acetoacetate , biginelli reaction , catalysis , organic chemistry , medicinal chemistry
Double axially chiral bisphosphorylimides have been used as catalysts in enantioselective Biginelli reactions. The three‐component reaction of aromatic aldehydes, thiourea, and ethyl acetoacetate took place by using 5 mol‐% catalyst in ethyl acetate at 50 °C. A series of chiral dihydropyrimidinethiones (DHPMs) were obtained in high yields (up to 97 %) with good to high enantioselectivities (up to 96 % ee ) in only 12 hours.