HEXACHLOROCYCLOPENTADIENE IN DIELS-ALDER ASYMMETRIC REACTION
TETRAHEDRON, cilt.50, sa.7, ss.2099-2106, 1994 (SCI-Expanded, Scopus)
- 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.