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

Date

2012-12-31

Author

Yazicioglu, Emre Y.
Tanyeli, Cihangir

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This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

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.

Subject Keywords

Dmap, Access, Bromides, Alkylamines, Derivatives, Phosphoramidite, Amination, Aryl iodides, Highly efficient, Kinetic resolution

URI

https://hdl.handle.net/11511/42128

Collections

Department of Chemistry, Article