Stereocontrol in Horner-Wadsworth-Emmons condensations of. alpha.-phosphono lactones with aldehydes: a synthesis of integerrinecic acid and senecic acid …

K Lee, JA Jackson, DF Wiemer

Index: Lee, Koo; Jackson, John A.; Wiemer, David F. Journal of Organic Chemistry, 1993 , vol. 58, # 22 p. 5967 - 5971

Full Text: HTML

Citation Number: 45

Abstract

The Horner-Wadsworth-Emmons condensations of a-phosphono lactones were investigated under a variety of conditions. Upon treatment with KHMDS and 18-crown-6 in THF, condensations of the five-membered ring phosphono lactones 7a and 8 with propionaldehyde afforded the E olefins cleanly. In contrast, these phosphonates gave predominantly the 2 olefins upon treatment with propionaldehyde, &Cos, and 18-crown-6 ...