A method for the synthesis of pyridine-based C-2-symmetrical chiral nucleophilic organocatalysts via Pd-catalyzed coupling

Yazicioglu E. Y., TANYELİ C.

TETRAHEDRON-ASYMMETRY, vol.23, no.24, pp.1694-1699, 2012 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 23 Issue: 24
  • Publication Date: 2012
  • Doi Number: 10.1016/j.tetasy.2012.11.007
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1694-1699
  • Middle East Technical University Affiliated: Yes


A one step Pd-catalyzed coupling methodology involving a reaction between a chiral diamine and a 2-bromo-4-(alkylamino)pyridine, was developed for the synthesis of novel C-2-symmmetrical chiral compounds with chemical yields of up to 87%. The organocatalytic performance was tested as an alternative to the enzymatic kinetic resolution of 1-phenylethanol and a promising result of 76% ee was obtained. We observed that the catalysts synthesized had their own characteristics in terms of enantioselectivity; for example, non-nucleophilic heterogeneous auxiliary bases and ether solvents proved to be more efficient. (C) 2012 Elsevier Ltd. All rights reserved.