Diels-Alder reaction of R-(-)-carvone with isoprene

Tony K.M. Shing, Ho Y. Lo, Thomas C.W. Mak

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Diels-Alder reactions of R-(-)-carvone with isoprene using different Lewis acids as catalysts have been studied. The best results were obtained with EtAlCl2 at 25 °C for 48 hours. The yields are quantitative and the d.e. is 86.8%. Regioselective dihydroxylation at the endocyclic double bond of the cycloadduct followed by acetonation gave a crystalline acetonide, the structure and stereochemistry of which were confirmed by an X-ray crystallographic analysis. Hence the stereochemical outcome of the Diels- Alder reaction is now established and the reaction occurred preponderantly in an anti orientation with respect to the isopropylene group in R-(-)-carvone.

Original languageEnglish
Pages (from-to)4643-4648
Number of pages6
JournalTetrahedron
Volume55
Issue number15
DOIs
Publication statusPublished - 1999 Apr 9

Keywords

  • Cycloadditions
  • Diels-Alder reactions
  • Terpenes and terpenoids

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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    Shing, T. K. M., Lo, H. Y., & Mak, T. C. W. (1999). Diels-Alder reaction of R-(-)-carvone with isoprene. Tetrahedron, 55(15), 4643-4648. https://doi.org/10.1016/S0040-4020(99)00145-3