A method for the synthesis of pyridine-based C2-symmetrical chiral nucleophilic organocatalysts via Pd-catalyzed coupling
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 C2-symmmetrical chiral compounds with chemical yields of up to 87%. The organocatalytic performance was tested as an alternative t...
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| Published in | Tetrahedron: asymmetry Vol. 23; no. 24; pp. 1694 - 1699 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
Elsevier Ltd
31.12.2012
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| Online Access | Get full text |
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| Summary: | 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 C2-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. |
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| ISSN: | 0957-4166 1362-511X |
| DOI: | 10.1016/j.tetasy.2012.11.007 |