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Chiral‐at‐Metal Rhodium(III) Complex Catalyzed Enantioselective Vinylogous Michael Addition of α , α ‐Dicyanoolefins with α , β ‐Unsaturated 2‐Acyl Imidazoles
Author(s) -
Hu Liangjian,
Lin Shaoxia,
Li Shiwu,
Kang Qiang,
Du Yu
Publication year - 2020
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201901590
Subject(s) - enantioselective synthesis , rhodium , michael reaction , catalysis , chemistry , organic chemistry , combinatorial chemistry
As a development of traditional vinylogous Michael addition reactions, catalytic enantioselective γ ‐functionalization of α , α ‐dicyanoolefins possesses a remarkable advantage in carboxylic derivatives synthesis and has emerged as a powerful tool for the preparation of high value chemicals. In another hand, the development of versatile and highly efficient catalyst is quite critical for such asymmetric transformations. Herein, a newly developed chiral‐at‐metal rhodium (III) complex catalyzed enantioselective vinylogous Michael addition of α , α ‐dicyanoolefins with α , β ‐unsaturated 2‐acyl imidazoles has been realized, delivering the corresponding adducts in 68−89 % yields with up to 95 % enantioselectivity. The reaction can be conducted on a gram‐scale using a low catalyst loading (0.5 mol %) without impacting its efficiency.