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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
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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.
Subject Keywords
Dmap
,
Access
,
Bromides
,
Alkylamines
,
Derivatives
,
Phosphoramidite
,
Amination
,
Aryl iodides
,
Highly efficient
,
Kinetic resolution
URI
https://hdl.handle.net/11511/42128
Journal
TETRAHEDRON-ASYMMETRY
DOI
https://doi.org/10.1016/j.tetasy.2012.11.007
Collections
Department of Chemistry, Article