Norbornanoid Chiral Ketones by Desymmetrization of Dibromoalkenes
HELVETICA CHIMICA ACTA, cilt.97, sa.4, ss.537-545, 2014 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 97 Sayı: 4
- Basım Tarihi: 2014
- Doi Numarası: 10.1002/hlca.201300191
- Dergi Adı: HELVETICA CHIMICA ACTA
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Sayfa Sayıları: ss.537-545
- Atatürk Üniversitesi Adresli: Evet
Özet
New optically active polycyclic ketones 6a-6d, amenable to a large variety of synthetic applications, have been prepared from readily available 2,3-dibromonorbornene and analogs (Scheme 2) via desymmetrization with (-)-ephedrine, followed by hydrolysis under mild acidic conditions. At variance with substrates 4a-4d, the sterically hindered norbornene derivative 4e reacts with the solvent N-methylpyrrolidin-2-one (NMP) leading to the formation of the unusual cyclopropanoid products 8a and 8b.