Next Article in Journal / Special Issue
Nucleophilic Benzoylation Using a Mandelic Acid Dioxolanone as a Synthetic Equivalent of the Benzoyl Carbanion. Oxidative Decarboxylation of α-Hydroxyacids
Previous Article in Journal / Special Issue
Masked ω-Lithio Ester Enolates: Synthetic Applications
Article Menu

Export Article

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

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

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
View Full-Text   |   Download PDF [219 KB, uploaded 18 June 2014]   |  

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).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

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.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top