A γ,δ-unsaturated amide, prepared by an amide acetal Claisen rearrangement, has been subjected to hydroxy-lactonisation, and reductive cleavage of the corresponding keto-lactone with aluminium amalgam has led to a trisubstituted cyclohexanone derivative with retention of configuration, thus establishing a new method for the stereocontrolled synthesis of 2,3,3-trisubstituted cyclohexanones.
P. M. Cairns, C. Howes, P. R. Jenkins, D. R. Russell and L. Sherry, J. Chem. Soc., Chem. Commun., 1984, 1487 DOI: 10.1039/C39840001487
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