Synthetic communications

Practical Stereoselective Synthesis of (2 E)??and (2 Z)??4??Cycloalkylidenebut??2??enoic Acids

SK Karagiozov, FS Abbott

Index: Karagiozov, Stoyan K.; Abbott, Frank S. Synthetic Communications, 2004 , vol. 34, # 5 p. 871 - 888

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Citation Number: 3

Abstract

Abstract Stereoselective synthesis of α, β??unsaturated esters 7 and 8 was achieved through Horner–Wadsworth–Emmons reaction of β, β??disubstituted α, β??unsaturated aldehydes. Thus, aldehydes 6 undergo olefination with phosphonate carbanion generated from triethyl phosphonoacetate 3 and lithium hydroxide or butyl lithium/DMPU to give (E)?螃?, β?? unsaturated esters 7 with excellent selectivity. The treatment of 6 with the new Horner– ...