Chiral Phosphoric Acid-Catalyzed Enantioselective Phospha-Michael-Type Addition Reaction of Diarylphosphine Oxides with Alkenyl Benzimidazoles
- 29 September 2020
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 85 (22), 14802-14809
- https://doi.org/10.1021/acs.joc.0c01840
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 corresponding chiral phosphine, which is potential benzimid-azole-based chiral P,N-ligands, without loss of enantiomeric excess.Keywords
Funding Information
- Ministry of Education, Culture, Sports, Science and Technology (JP17H06447)
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