Enantioselective aza Michael-type addition to alkenyl benzimidazoles catalyzed by a chiral phosphoric acid

Ya Yi Wang, Kyohei Kanomata, Toshinobu Korenaga, Masahiro Terada

研究成果: Article査読

34 被引用数 (Scopus)

抄録

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. Heterocycle squared: Highly enantioselective Michael-type addition reactions to alkenyl benzimidazoles with pyrazoles and indazoles as nitrogen nucleophiles are accomplished using a chiral phosphoric acid catalyst. Theoretical studies elucidated the reaction pathway and the origin of the stereochemical outcome. The catalyst substituent and the N-protecting group (PG) of the benzimidazole contribute to the resulting high enantioselectivity.

本文言語English
ページ(範囲)927-931
ページ数5
ジャーナルAngewandte Chemie - International Edition
55
3
DOI
出版ステータスPublished - 2016 1 18

ASJC Scopus subject areas

  • 触媒
  • 化学 (全般)

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