Journal of the American Chemical Society 2005-08-31

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

Tsuneo Imamoto, Keitaro Sugita, Kazuhiro Yoshida

Index: J. Am. Chem. Soc. 127 , 11934, (2005)

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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.