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

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Author(s): Rafael Chinchilla | Patricia Mazón | Carmen Nájera

Journal: Molecules
ISSN 1420-3049

Volume: 9;
Issue: 5;
Start page: 349;
Date: 2004;
Original page

Keywords: Amino acids | asymmetric synthesis | phase-transfer catalysis | chiral ammonium salts.

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.
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