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Synlett 1996; 1996(11): 1115-1116
DOI: 10.1055/s-1996-5667
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A New Two Steps Synthesis of α-Substituted γ-Methyl γ-Lactones from Nitroalkanes

R. Ballini* , G. Bosica
  • *Dipartimento di Scienze Chimiche dell’Università, Via S. Agostino n.1, 62032 Camerino (MC), Italy, Fax. +39(737)637345, e-mail ballini@camvax.unicam.it
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Publication Date:
31 December 2000 (online)

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α-Substituted γ-methyl γ-lactones are efficiently prepared, in two steps, by regiospecific Michael addition of nitroalkanes to methyl trans-4-oxo-2-pentenoate in MeCN/DBU followed by chemoselective reduction of the obtained enones with NiCl2⋅6H2O/NaBH4. By this method a variety of functionalized 3,5-disubstituted butyrolactones can be obtained.

Nitroalkanes - trans-4-oxo-2-pentenoate - α-substituted γ-methyl γ-lactones - Michael addition - nickel boride

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