Synlett

Indium-Mediated Allylation of the N, N-Dimethyl Glyoxal Mono-Hydrazone: One-Pot Synthesis of Bis-Homoallyl, and of Homoallyl-Alkyl 1, 2-Diols

V Cerè, F Peri, S Pollicino, A Ricci

Index: Cere, Vanda; Peri, Francesca; Pollicino, Salvatore; Ricci, Alfredo Synlett, 1999 , # 10 p. 1585 - 1587

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Citation Number: 10

Abstract

Abstract: Hydrazones behave as highly reactive species in the allylation under Barbier conditions. Nucleophilic addition of an alkyllithium to the carbonyl moiety of the glyoxal mono-hydrazone followed by indium-mediated allylation, leads in high yields to bisfunctionalized 1, 2-diols in a one-pot two-step reaction. Key words: glyoxal, hydrazone, indium, allylation, alkylation