Novel enantioselective synthesis of both enantiomers of furan-2-yl Amines and amino acids

Demir A., Sesemoglu O., Ulku D., Arici C.

HELVETICA CHIMICA ACTA, cilt.86, sa.1, ss.91-105, 2003 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 86 Sayı: 1
  • Basım Tarihi: 2003
  • Doi Numarası: 10.1002/hlca.200390022
  • Dergi Adı: HELVETICA CHIMICA ACTA
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.91-105
  • Hacettepe Üniversitesi Adresli: Hayır

Özet

A new enantioselective synthesis of furan-2-yl amines and amino acids is described, in which the key step is the oxazaborolidine-catalyzed enantioselective reduction of O-benzyl (E)- and (Z)-furan-2-yl ketone oximes to the corresponding chiral amines. The chirality of the furan-2-yl amines is fully controlled by the appropriate choice of the geometrical isomer of the O-benzyl oxime. Oxidation of the furan ring furnished amino acids in high yields.