Chiral phosphoric acid-catalyzed enantioselective phospha-michael-type addition reaction of diarylphosphine oxides with alkenyl benzimidazoles

Linan Hou, Jun Kikuchi, Haiting Ye, Ming Bao, Masahiro Terada

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

An enantioselective phospha-Michael-type addition reaction of diarylphosphine oxides with alkenyl benzimidazoles was demonstrated using a chiral phosphoric acid as the chiral Brønsted acid catalyst. Addition products having phosphorus and benzimidazole units were formed in high yields with excellent enantioselectivities in most cases. The reduction of the phosphine oxide unit in the addition product afforded the corresponding chiral phosphine, which is a potential benzimidazole-based chiral P,N-ligand, without loss of enantiomeric excess.

Original languageEnglish
Pages (from-to)14802-14809
Number of pages8
JournalJournal of Organic Chemistry
Volume85
Issue number22
DOIs
Publication statusPublished - 2020 Nov 20

ASJC Scopus subject areas

  • Organic Chemistry

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