HEXACHLOROCYCLOPENTADIENE IN DIELS-ALDER ASYMMETRIC REACTION

AKHMEDOV I., PEYNIRCIOGLU B., MAMEDOV E., TANYELI C., DEMIR A.

TETRAHEDRON, vol.50, no.7, pp.2099-2106, 1994 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 50 Issue: 7
  • Publication Date: 1994
  • Doi Number: 10.1016/s0040-4020(01)85072-9
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.2099-2106
  • Middle East Technical University Affiliated: Yes

Abstract

Asymmetric thermal Diels-Alder reactions with chiral dienophiles l-menthyl acrylate and l-menthyl allyl ether, using hexachlorocyclopentadiene (HCC) gave cycloadducts of up to 15%ee. Milder reaction conditions achieved by the use of Lewis acid catalysis increased the optical yields up to 2.8 fold. The catalyzed and uncatalyzed reactions using l-menthyl acrylate result in the formation of adducts having opposite configurations. The products have also been resolved via diastereomer formation as pure enantiomers.