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

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

Research output: Contribution to journalArticle

27 Citations (Scopus)

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. 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.

Original languageEnglish
Pages (from-to)927-931
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number3
DOIs
Publication statusPublished - 2016 Jan 18

Keywords

  • Michael additions
  • enantioselectivity
  • heterocycles
  • organocatalysis
  • synthetic methods

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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