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
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.
Topics & Concepts
ChemistryEnantioselective synthesisPhosphoric acidPhosphine oxideBenzimidazolePhosphineCatalysisMichael reactionOrganic chemistryEnantiomeric excessEnantiomerMedicinal chemistryAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and CatalysisChemical Synthesis and Analysis