Highly Z-Selective Synthesis of Disubstituted. ALPHA.,. BETA.-Unsaturated Cyanides and Amides Using 10-P-5 Wittig Type Reagents.

S Kojima, K Kawaguchi, S Matsukawa, K Uchida…

Index: Kojima, Satoshi; Kawaguchi, Kazuhiro; Matsukawa, Shiro; Uchida, Keiichiro; Akiba, Kin-ya Chemistry Letters, 2002 , # 2 p. 170 - 171

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Citation Number: 8

Abstract

Phosphoranes (10-P-5) bearing cyanomethyl, acetamide, and N, N-dimethylacetamide groups were examined for Wittig type reactions. All three reacted to give the corresponding olefins. The reaction of the cyanomethyl reagent with aldehydes gave α, β-unsaturated cyanides with high Z-selectivity in the case of aliphatic aldehydes (Z: E= 94: 6 to 99: 1). On the other hand, the reactions of the two amide reagents with aldehydes yielded α, β- ...