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

作者：Yazicioglu Emre Y; Tanyeli Cihangir^*

来源：Tetrahedron: Asymmetry , 2012, 23(24): 1694-1699.

DOI：10.1016/j.tetasy.2012.11.007

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.

• 出版日期2012-12-31