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Synthesis 2000; 2000(2): 295-299
DOI: 10.1055/s-2000-6257
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A Simplified Route to (E)-2-Alkylidene-1,4-diketones

Ahlem Chamakh* , Mustapha M'hirsi, Jean Villiéras, Jacques Lebreton, Hassen Amri
  • *Laboratoire de Chimie Organique et Organométallique, Faculté des Sciences, Campus Universitaire, 1060-Tunis-Tunisia; Fax +2 16 (1) 88 50 08; E-mail: hassen.Amri@fst.rnu.tn
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Publication Date:
31 December 2000 (online)

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Conjugate addition of nitroalkanes to allyl Baylis-Hillman acetates 1 in the presence of NaOH (0.6 N) in THF gave 2-alkylidene-4-nitro ketones 2 with total stereoselectivity, which were further converted via the Nef reaction into the corresponding 1,4-diketones 3 in fair to good yields.

Baylis-Hillman products - Nef reaction - 2-alkylidene-1,4-diketones - addition reactions - tandem reactions - hydrolysis - cyclizations