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

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

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被引用次数: 45

摘要

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 ...