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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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

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Citation Formats

E. Y. Yazicioglu and C. Tanyeli, “A method for the synthesis of pyridine-based C-2-symmetrical chiral nucleophilic organocatalysts via Pd-catalyzed coupling,” TETRAHEDRON-ASYMMETRY, pp. 1694–1699, 2012, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/42128.