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A new class of asymmetric phase-transfer catalysts derived from Cinchona alkaloids — Application in the enantioselective synthesis of α-amino acids

✍ Scribed by Barry Lygo; Philip G. Wainwright

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
247 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

A new class of Cinchona alkaloid-derived quaternary ammonium phase-transfer catalysts bearing a N-anthracenylmethyl function ate presented. These catalysts show high stereocontrol in the asynunetric alkylation of a benzophenone-derived glycine-imine, and application of this process to the enantioselective synthesis of a range of a-amino acid esters (e.e. 67-94%) is investigated.

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Poly(ethylene glycol) supported cinchona
Poly(ethylene glycol) supported cinchona alkaloids as phase transfer catalysts: application to the enantioselective synthesis of α-amino acids
✍ Baptiste Thierry; Jean-Christophe Plaquevent; Dominique Cahard 📂 Article 📅 2003 🏛 Elsevier Science 🌐 English ⚖ 193 KB

We have demonstrated that quaternary ammonium salts of cinchona alkaloids grafted to a poly(ethylene glycol) matrix are efficient homogeneous catalysts in the enantioselective alkylation of glycine Schiff base derivatives. The role of the solvent, the molecular weight of the polymer and the anchorag