Tetrahedron letters

Water-mediated transition-metal-free Tsuji–Trost-type reaction

C Chevrin, J Le Bras, F Hénin, J Muzart

Index: Chevrin, Carole; Le Bras, Jean; Henin, Francoise; Muzart, Jacques Tetrahedron Letters, 2003 , vol. 44, # 44 p. 8099 - 8102

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Citation Number: 30

Abstract

The treatment of 1-acetoxy-1, 3-diphenylpropene (1) by C-, O-, S-and N-nucleophiles in basic aqueous media produced the corresponding substitution products in the absence of a transition-metal catalyst. Mechanistic studies, using (S)-1 and p-MeC6H4CH (OAc) CH CHPh as substrates, led to propose a BAL1 cleavage of the ester function leading to a stabilized allylic carbocation as intermediate.