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

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

研究成果: Article査読

7 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)4643-4648
ページ数6
ジャーナルTetrahedron
55
15
DOI
出版ステータスPublished - 1999 4 9

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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