Diastereoselectivity in the Horner-Wittig reaction: X-ray crystal structure of 2-(1RS,2SR)-diphenylphosphinoyl-1-phenylpropan-1-ol

Abstract

Ethyldiphenylphosphine oxide reacts with butyl-lithium and benzaldehyde to give the title compound which eliminates diphenylphosphinate ion in base to give Z-1 -phenylpropene. The elimination is stereo-specific and syn. The (1RS,2RS) isomer, prepared by sodium borohydride reduction of the corresponding ketone, gives E-1 -phenylpropene.