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, vol.86, no.1, pp.91-105, 2003 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 86 Issue: 1
  • Publication Date: 2003
  • Doi Number: 10.1002/hlca.200390022
  • Journal Name: HELVETICA CHIMICA ACTA
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.91-105
  • Middle East Technical University Affiliated: Yes

Abstract

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.