A practical deca-gram scale ring expansion of (R)-(−)-carvone to (R)-(+)-3-methyl-6-isopropenyl- cyclohept-3-enone-1

    • Leandro de C. Alvesa
    • André L. Desideráa
    • Kleber T. de Oliveiraa
    • Sean Newtonb
    • Steven V. Ley* b
    • Timothy J. Brocksom* a
    • a Departamento de Química, Universidade Federal de São Carlos, P.O. Box 676, São Carlos – SP, Brazil
    • b Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, UK
    A practical deca-gram scale ring expansion of (R)-(−)-carvone to (R)-(+)-3-methyl-6-isopropenyl- cyclohept-3-enone-1

    A route to enantiopure (R)-(+)-3-methyl-6-isopropenyl-cyclohept-3-enone-1, an intermediate for terpenoids, has been developed and includes a highly chemo- and regioselective Tiffeneau–Demjanov reaction. Starting from readily available (R)-(−)-carvone, this robust sequence is available on a deca-gram scale and uses flow chemistry for the initial epoxidation reaction. The stereochemistry of the addition of two nucleophiles to the carbonyl group of (R)-(−)-carvone has been determined by X-ray diffraction studies and chemical correlation.

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