Norbornanoid Chiral Ketones by Desymmetrization of Dibromoalkenes

Koçak R., BORSATO G., DE LUCCHI O., DAŞTAN A.

HELVETICA CHIMICA ACTA, cilt.97, sa.4, ss.537-545, 2014 (SCI-Expanded) identifier identifier

  • 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.