Soluble Polymer Supported Synthesis of α-Amino Acid Derivatives | Zendy

Bérengère Sauvagnat | Zendy; Katarzyna Kulig | Zendy; Frédéric Lamaty | Zendy; René Lazaro | Zendy; Jean Martínez | Zendy

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Soluble Polymer Supported Synthesis of α-Amino Acid Derivatives

Author(s) -

Bérengère Sauvagnat,

Katarzyna Kulig,

Frédéric Lamaty,

René Lazaro,

Jean Martínez

Publication year - 2000

Publication title -

journal of combinatorial chemistry

Language(s) - English

Resource type - Journals

eISSN - 1520-4774

pISSN - 1520-4766

DOI - 10.1021/cc9900605

Subject(s) - electrophile , chemistry , alkylation , reagent , polymer , ethylene glycol , catalysis , transfer agent , polymer chemistry , peg ratio , acetonitrile , organic chemistry , combinatorial chemistry , copolymer , finance , economics

A Schiff base activated glycine supported on a soluble polymer (poly(ethylene glycol) (PEG)) was readily alkylated with a wide variety of electrophiles in the presence of a carbonate base in acetonitrile. The presence of the polymer provided a phase-transfer catalysis environment which accelerated the reaction. Effects of various carbonate bases and leaving groups have been also studied. Completion of the PEG-supported reaction was obtained without using a large excess of reagents or an extra phase-transfer catalyst, even in the case of unreactive or hindered electrophiles. After cleavage from the polymer, alpha-amino esters are obtained in good yields.

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