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Synlett 1999; 1999(10): 1585-1587
DOI: 10.1055/s-1999-2881
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Indium-Mediated Allylation of the N,N-Dimethyl Glyoxal Mono-Hydrazone: One-Pot Synthesis of Bis-Homoallyl, and of Homoallyl-Alkyl 1,2-Diols

Vanda Cerè* , Francesca Peri, Salvatore Pollicino, Alfredo Ricci
  • *Department of Organic Chemistry, "A. Mangini"-University of Bologna, Via Risorgimento 4, 40124 Bologna, Italy; Fax + 39 5 12 09 36 54; E-mail: ricci@ms.fci.unibo.it
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Publication Date:
31 December 1999 (online)

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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 bis-functionalized 1,2-diols in a one-pot two-step reaction.

glyoxal - hydrazone - indium - allylation - alkylation

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