Unprecedented. gamma.-selective nucleophilic substitution reaction of allylmetal reagents: a new cross-coupling of diphenyl phosphates with allylic Grignard reagents

A Yanagisawa, H Hibino, N Nomura…

Index: Yanagisawa, Akira; Hibino, Hiroaki; Nomura, Nobuyoshi; Yamamoto, Hisashi Journal of the American Chemical Society, 1993 , vol. 115, # 13 p. 5879 - 5880

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Citation Number: 20

Abstract

Most allylmetal reagents combine with carbonyl compounds by the SE~'pathway to afford homoallylic alcohols selectively (Type I, Scheme I). l A method described previously permits selective coupling with carbonyl compounds at the a-position (Type 11) using allylbarium reagent. 2 The same reagent reacts with alkyl halides to give a-alkylation product almost exclusively (Type III). 3 We shall first describe a new selective coupling of Type IV, the ...