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Chiral Primary Amine Catalyzed Asymmetric Epoxidation of α‐Substituted Acroleins
Author(s) -
Li Jiuyuan,
Fu Niankai,
Zhang Long,
Zhou Pengxin,
Luo Sanzhong,
Cheng JinPei
Publication year - 2010
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.201001117
Subject(s) - chemistry , catalysis , primary (astronomy) , amine gas treating , alkene , vicinal , diamine , enantioselective synthesis , yield (engineering) , organic chemistry , combinatorial chemistry , medicinal chemistry , physics , materials science , astronomy , metallurgy
1,1‐Disubstituted terminal alkenes remain challenging substrates in asymmetric epoxidation reactions. In this study, chiral primary amines are shown to catalyze the asymmetric epoxidation of α‐substituted acroleins, a versatile type of 1,1‐disubstituted terminal alkene. Among various chiral primary amines explored, the chiral primary‐tertiary vicinal diamine derived from trans ‐1,2‐diphenylethane‐1,2‐diamine is identified as the optimal catalyst, which, in combination with 5‐sulfosalicyclic acid (5‐SSA), exhibits good catalytic activity (up to 95 % yield) and enantioselectivity (up to 88 % ee ). Aqueous 2 M sodium chloride was found to be the optimal reaction media.