HEXACHLOROCYCLOPENTADIENE IN DIELS-ALDER ASYMMETRIC REACTION

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

TETRAHEDRON, cilt.50, sa.7, ss.2099-2106, 1994 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 50 Sayı: 7
  • Basım Tarihi: 1994
  • Doi Numarası: 10.1016/s0040-4020(01)85072-9
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.2099-2106
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

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.