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An Asymmetric Organocatalytic Approach to Michael Reactions of Thiazolones and Nitroalkenes: Preparation of Compounds with Anti‐Cancer Potency
Author(s) -
Liu Xiaodong,
Song Hongjin,
Chen Qiao,
Li Wenyi,
Yin Wen,
Kai Ming,
Wang Rui
Publication year - 2012
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.201201094
Subject(s) - stereocenter , chemistry , thiourea , michael reaction , enantioselective synthesis , amine gas treating , catalysis , quaternary carbon , organocatalysis , potency , tertiary amine , combinatorial chemistry , carbon fibers , organic chemistry , in vitro , biochemistry , materials science , composite number , composite material
We present a highly efficient strategy for obtaining a series of chiral 2,4‐disubstituted thiazolone derivatives with excellent diastereo‐ and enantioselectivities through the creation of carbon‐ and nitrogen‐substituted quaternary carbon stereocenters. With the chiral tertiary amine‐thiourea catalyst developed by our group, the reactions could be performed smoothly at 1 mol‐% catalyst loadings without any additive. Preliminary biological evaluation demonstrated that these analogues could inhibit cell proliferation in vitro significantly.