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A Straightforward Three-Component Synthesis of α-Amino Esters Containing a Phenylalanine or a Phenylglycine Scaffold

Caroline Haurena, Erwan Le Gall, Stéphane Sengmany, Thierry Martens and Michel Troupel

*Électrochimie et Synthèse Organique, Institut de Chimie et des Matériaux Paris Est (ICMPE), UMR 7182 CNRS, Université Paris Est Créteil Val-de-Marne, 2-8 rue Henri Dunant, 94320 Thiais, France, Email: legallglvt-cnrs.fr

C. Haurena, E. Le Gall, S. Sengmany, T. Martens, M. Troupel, J. Org. Chem., 2010, 75, 2645-2650.

DOI: 10.1021/jo1002328 (free Supporting Information)


Abstract

A straightforward three-component reaction of preformed aromatic or in situ generated benzylic organozinc reagents with amines and ethyl glyoxylate allows the synthesis of a range of α-amino esters in very good yields. The procedure, which is characterized by its simplicity, allows the concise synthesis of esters bearing a phenylglycine or a phenylalanine scaffold.

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An Expedient Three-Component Synthesis of Tertiary Benzylamines

E. Le Gall, A. Decompte, T. Martens, M. Troupel, Synthesis, 2010, 249-254.


Key Words

α-Amino Esters (Amination, Coupling), Zinc, Multicomponent Reaction


ID: J42-Y2010-0990