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Enatioselective Chalcogeno‐Baylis‐Hillman Reaction of Arylaldehydes with MVK and Acrylates Catalyzed by Chiral Thiepin‐TiCl 4 Complex
Author(s) -
Yin Yan,
Sun Guofeng,
Zhang Heng,
Zhou Hong,
Wu Fanhong
Publication year - 2014
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201400077
Subject(s) - methyl vinyl ketone , chemistry , thiophene , catalysis , lewis acids and bases , ketone , optically active , organic chemistry , baylis–hillman reaction , medicinal chemistry , combinatorial chemistry
In a rational chiral molecular design of chalcogenides, optically active thiepin with C 2 ‐symmetric chirality was synthesized from commercially available thiophene. Then enatioselective Chalcogeno‐Baylis‐Hillman reactions of arylaldehydes with methyl vinyl ketone (MVK) and acrylates were investigated in the presence of thiepin‐Lewis acid complex. Finally, up to 64% ee was achieved in the presence of 0.2 equiv. of ( S )‐thiepin at 20°C.