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

Tony Kung Ming 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
Externally publishedYes

Fingerprint

Cycloaddition Reaction
Lewis Acids
Stereochemistry
X-Rays
Crystalline materials
X rays
Catalysts
isoprene
carvone
dichloroethylaluminum

Keywords

  • Cycloadditions
  • Diels-Alder reactions
  • Terpenes and terpenoids

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

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

Diels-Alder reaction of R-(-)-carvone with isoprene. / Shing, Tony Kung Ming; Lo, Ho Y.; Mak, Thomas C.W.

In: Tetrahedron, Vol. 55, No. 15, 09.04.1999, p. 4643-4648.

Research output: Contribution to journalArticle

Shing, TKM, Lo, HY & Mak, TCW 1999, 'Diels-Alder reaction of R-(-)-carvone with isoprene', Tetrahedron, vol. 55, no. 15, pp. 4643-4648. https://doi.org/10.1016/S0040-4020(99)00145-3
Shing, Tony Kung Ming ; Lo, Ho Y. ; Mak, Thomas C.W. / Diels-Alder reaction of R-(-)-carvone with isoprene. In: Tetrahedron. 1999 ; Vol. 55, No. 15. pp. 4643-4648.
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