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The Stereochemistry of Organometallic Compounds. XXV The Stereochemistry of Displacements of Secondary Methanesulfonate and p-Toluenesulfonate Esters by Diphenylphosphide Ions. X-Ray Crystal Structure of (5α-Cholestan-3α-yl)diphenylphosphine Oxide
Jackson, W. Roy,Thomson, Robin J.,Mackay, Maureen F.
, p. 111 - 118 (2007/10/02)
Reactions of both axial and equatorial cholestan-3α- and -3β-yl mesylates and tosylates with sodium diarylphosphides give cholestanylphosphines in good yield and with complete inversion of stereochemistry.The stereochemistry has been established by an X-ray crystal structure of (5α-cholestan-3α-yl)diphenylphosphine oxide, and a general method for distinguishing between axial and equatorial phosphines based on 31P n.m.r. spectra is presented.The monophosphines were used as ligands in asymmetric hydrogenation, but only low optical yields were obtained.
