An air-stable P-chiral phosphine ligand for highly enantioselective transition-metal-catalyzed reactions

Tsuneo Imamoto; Keitaro Sugita; Kazuhiro Yoshida

doi:10.1021/ja053458f

An air-stable P-chiral phosphine ligand for highly enantioselective transition-metal-catalyzed reactions

J Am Chem Soc. 2005 Aug 31;127(34):11934-5. doi: 10.1021/ja053458f.

Authors

Tsuneo Imamoto¹, Keitaro Sugita, Kazuhiro Yoshida

Affiliation

¹ Department of Chemistry, Faculty of Science, Chiba University, Chiba 263-8522, Japan. imamoto@faculty.chiba-u.jp

PMID: 16117520
DOI: 10.1021/ja053458f

Abstract

A new P-chiral phosphine ligand, (R,R)-2,3-bis(tert-butylmethylphosphino)quinoxaline, has been prepared by the reaction of enantiomerically pure tert-butylmethylphosphine-borane with 2,3-dichloroquinoxaline. This ligand, in contrast to most of the previously reported P-chiral ligands, is an air-stable solid and exhibits excellent enantioselectivities in both Rh-catalyzed asymmetric hydrogenations and Rh- or Pd-catalyzed carbon-carbon bond-forming reactions.