A bis-Lewis basic 2-aminoDMAP/prolinamide organocatalyst for application to the enantioselective synthesis of Warfarin and derivatives

IŞIK M., Akkoca H. U., Akhmedov I. M., TANYELİ C.

TETRAHEDRON-ASYMMETRY, vol.27, pp.384-388, 2016 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 27
  • Publication Date: 2016
  • Doi Number: 10.1016/j.tetasy.2016.04.001
  • Journal Name: TETRAHEDRON-ASYMMETRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.384-388
  • Middle East Technical University Affiliated: Yes

Abstract

A new chiral sec-amine/amidine-base hybrid catalyst, 2-aminoDMAP/prolinamide, is reported, which is able to catalyze conjugate addition of 4-hydroxycoumarin and various benzylideneacetones, a reaction that directly gives anticoagulant Warfarin and its analogues, with good yields (70-87%) and enantioselectivities (58-72%). (C) 2016 Elsevier Ltd. All rights reserved.