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, UKRead the publication that featured this abstract
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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