Tetrahedron letters

Metal zinc-promoted gem-bisallylation of acid chlorides with allyl chlorides in the presence of chlorotrimethylsilane

Y Ishino, M Mihara, M Kageyama

Index: Ishino, Yoshio; Mihara, Masatoshi; Kageyama, Manabu Tetrahedron Letters, 2002 , vol. 43, # 37 p. 6601 - 6604

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Citation Number: 16

Abstract

Treatment of acid chlorides (2) with allyl chlorides (1) in the presence of zinc dust and a catalytic amount of chlorotrimethylsilane (TMSCl) in THF brought about highly facile and effective coupling to give the corresponding gem-bisallylation products, 4-hydroxy-penta-1, 6-dienes (3), in good to excellent yields. These reactions are assumed to proceed through allylzinc intermediates generated in situ.