THE WITTIG REACTION OF NON-STABILIZED PHOSPHORUS YLIDES AND AROMATIC ALDEHYDES. STUDIES ON ERYTHRO AND THREO β-HYDROXYPHOSPHONIUM SALTS AND THE PROMOTION OF STEREOCHEMICAL DRIFT BY SYNERGISM BETWEEN DIASTEREOMERS

Article abstract of DOI:10.1016/S0040-4039(00)98758-6

In deprotonation studies with isomerically pure erythro-3 and threo-3, "retro-Wittig" reaction was only detected for erythro-3.Mixtures of erythro-3 and threo-3, under lithium salt-free conditions, undergo stereochemical drift because of synergism between diastereomeric oxaphosphetanes cis-2 and trans-2 during their decomposition to alkenes.