Synthesis of gamma-hydroxy-alpha,beta-unsaturated esters and nitriles from chiral cyanohydrins

摘要

The Horner-Wittig reaction of cyanomethyl- and carbethoxymethyl diphenyrphosphine oxides with a range of O-protected chiral alpha-hydroxy aldehydes is described. The alpha-hydroxy aldehydes were prepared with high enantiomeric purity from chiral O-protected cyanohydrins. The gamma-hydroxy-alpha,beta-unsaturated compounds formed were isolated in high enantiomeric purity and excellent yield. In all cases complete E-selectivity was observed. (C) 2000 Elsevier Science Ltd All rights reserved. [References: 19]