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Molecules 2004, 9(5), 349-364; doi:10.3390/90500349
Article

Polymer-Supported Cinchona Alkaloid-Derived Ammonium Salts as Recoverable Phase-Transfer Catalysts for the Asymmetric Synthesis of α-Amino Acids

,  and *
Departamento de Química Orgánica and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain
* Author to whom correspondence should be addressed.
Received: 2 March 2004 / Accepted: 22 March 2004 / Published: 30 April 2004
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Abstract

Alkaloids such as cinchonidine, quinine and N-methylephedrine have been N-alkylated using polymeric benzyl halides or co-polymerized and then N-alkylated, thus affording a series of polymer-supported chiral ammonium salts which have been employed as phase-transfer catalysts in the asymmetric benzylation of an N-(diphenylmethylene)glycine ester. These new polymeric catalysts can be easily recovered by simple filtration after the reaction and reused. The best ee’s were achieved when Merrifield resin-anchored cinchonidinium ammonium salts were employed.
Keywords: Amino acids; asymmetric synthesis; phase-transfer catalysis; chiral ammonium salts. Amino acids; asymmetric synthesis; phase-transfer catalysis; chiral ammonium salts.
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Chinchilla, R.; Mazón, P.; Nájera, C. Polymer-Supported Cinchona Alkaloid-Derived Ammonium Salts as Recoverable Phase-Transfer Catalysts for the Asymmetric Synthesis of α-Amino Acids. Molecules 2004, 9, 349-364.

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