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Enantioselective Aza Michael‐Type Addition to Alkenyl Benzimidazoles Catalyzed by a Chiral Phosphoric Acid
Author(s) -
Wang YaYi,
Kanomata Kyohei,
Korenaga Toshinobu,
Terada Masahiro
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201508231
Subject(s) - enantioselective synthesis , phosphoric acid , benzimidazole , substituent , chemistry , michael reaction , nucleophile , catalysis , organic chemistry , combinatorial chemistry
Abstract Highly enantioselective Michael‐type addition (MTA) reactions between N‐protected alkenyl benzimidazoles and either pyrazoles or indazoles as nitrogen nucleophiles are accomplished for the first time using chiral phosphoric acid catalyst. Theoretical studies elucidated the reaction pathway and the origin of the stereochemical outcomes, where the catalyst substituent and the N‐protecting group of benzimidazole contributed to the resulting high enantioselectivity.