Synthesis and asymmetric catalytic activity of (1S,1 ' S)-4,4 '-biquinazoline-based primary amines

ÇAKICI M., CATIR M., Karabuga S., Ulukanli S., KILIÇ H.

TETRAHEDRON-ASYMMETRY, vol.22, no.3, pp.300-308, 2011 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 22 Issue: 3
  • Publication Date: 2011
  • Doi Number: 10.1016/j.tetasy.2011.01.009
  • Journal Name: TETRAHEDRON-ASYMMETRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.300-308
  • Ataturk University Affiliated: Yes

Abstract

A series of (1S,1'S)-4,4'-biquinazoline-based primary amines were prepared from natural amino acids via a six-step reaction sequence of protection and condensation followed by key synthetic steps including chlorination, nickel(0)-mediated homocoupling, and deprotection. These novel amines were screened for the asymmetric ethylation of aryl aldehydes to yield alcohols with an (S)-configuration with enantiomeric excesses (ee) varying from 2% to 95%. (C) 2011 Elsevier Ltd. All rights reserved.