The first stereoselective synthesis of chiral halogenophosphines: optically active tert-butyl(phenyl)chlorophosphine

Abstract

The reaction of optically active tert-butyl(phenyl)(methylthio)chlorophosphonium trifluoromethanesulfonate 1 with tris(N,N-dimethylamino)phosphine at low temperature was found to give, stereoselectively, optically active tert-butyl(phenyl)chlorophosphine; when the salt 1 was treated with triphenylphosphine optically active tert-butyl(phenyl)chlorophosphine and methyl tert-butyl(phenyl)phosphinothioite were obtained as the result of the respective desulfurization and dehalogenation processes.