Cinchona alkaloid-based polymer-bound phase-transfer catalysts: efficient enantioselective alkylation of benzophenone imine of glycine esters.
Cross-linked polystyrene-bound and poly(ethylene glycol)-bound phase-transfer catalysts as well as homopolymers of cinchona alkaloid derivatives have been synthesised. Both soluble and insoluble polymers have been investigated. The enantioselective alkylation of N-diphenyl methylene glycine t-butyl ester has been successfully carried out in heterogeneous and homogeneous systems. High enantioselectivities (up to 96%) have been obtained. The polymer-bound catalysts have been easily recovered and conditions for efficient recycling have been studied.
Thierry
Baptiste
B
UMR 6014 CNRS de l'Institut de Recherche en Chimie Organique Fine, Université de Rouen, 1 Rue Tesnière, 76821, Mont Saint Aignan Cedex, France
Plaquevent
Jean-Christophe
JC
Cahard
Dominique
D
D000478:Alkylation; D001577:Benzophenones / Q000737:chemistry*; D002384:Catalysis; D002930:Cinchona Alkaloids / Q000138:chemical synthesis / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D004952:Esters / Q000737:chemistry*; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry; D007097:Imines; D011092:Polyethylene Glycols; D011108:Polymers / Q000737:chemistry*; D011137:Polystyrenes; D013237:Stereoisomerism
D001577:Benzophenones; D002930:Cinchona Alkaloids; D004952:Esters; D007097:Imines; D011108:Polymers; D011137:Polystyrenes; D011092:Polyethylene Glycols; C042193:glycine tert-butyl ester; C047723:benzophenone; D005998:Glycine