Allylic alkylation: Nature of the nucleophile and application to prenylation

BM Trost, L Weber, P Strege, TJ Fullerton…

Index: Trost,B.M. et al. Journal of the American Chemical Society, 1978 , vol. 100, p. 3426 - 3435

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Citation Number: 91

Abstract

Abstract: Alkylation of a-allylpalladium complexes requires a" soft" nucleophile. Successful alkylating agents include the anions derived from malonate,@-keto sulfones,@-keto sulfoxides, and 6-keto sulfides. The regioselectivity as a function of nucleophile is considered. The use of sulfur stabilized anions has proven quite versatile. The sulfone ester can lead to the addition at an allylic position of an acetate by mild desulfonylation or an ...

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