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Copper‐catalyzed asymmetric 1,4‐conjugate addition of dialkylzinc to enones
Author(s) -
Gou Shaohua,
Ye Zhongbin,
Shi Leiting,
Qing Dayong,
Zhang Wen,
Wang Yuliang
Publication year - 2010
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.1651
Subject(s) - chemistry , chalcone , diethylzinc , catalysis , enone , conjugate , yield (engineering) , dimethylzinc , copper , addition reaction , organic chemistry , medicinal chemistry , enantioselective synthesis , mathematical analysis , materials science , mathematics , metallurgy
Abstract Asymmetric 1,4‐conjugation addition of dialkylzinc (diethylzinc and dimethylzinc) to cyclic enones, chalcone and nitroalkenes was achieved by a 25 mol% ( R )‐6,6′‐Br 2 ‐BINOL( 1f ), 25 mol% CuSPh and 100 mol% dicyclohexylmethylamin(Cy 2 NMe) catalyst system. The Cu(I) catalyst system enables the cyclic enone, chalcone and nitroalkene generality with high enantioselectivity (up to 84% ee) and isolated yield (up to 94%) under mild reaction conditions. Copyright © 2010 John Wiley & Sons, Ltd.