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Access to Enantioenriched α-Amino Esters via Rhodium-Catalyzed 1,4-Addition/Enantioselective Protonation

Laure Navarre, Rémi Martinez, Jean-Pierre Genet* and Sylvain Darses*

*Laboratoire de Synthèse Sélective Organique (UMR 7573, CNRS), Ecole Nationale Supérieure de Chimie de Paris, 11 rue P&M Curie, 75231 Paris cedex 05, France, Email: jean-pierre-genetenscp.fr, sylvain-darsesenscp.fr

L. Navarre, R. Martinez, J.-P. Genet, S. Darses, J. Am. Chem. Soc., 2008, 130, 6159-6169.

DOI: 10.1021/ja710691p


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Abstract

Rhodium-catalyzed conjugate addition of potassium trifluoro(organo)borates to dehydroalanine derivatives, using chiral ligands such as fluorophos and in situ enantioselective protonation with guaiacol (2-methoxyphenol), afforded a variety of protected α-amino esters with high yields and enantiomeric excesses up to 95%.

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Efficient Access to Alanine Derivatives by 1,4-Additions of Potassium Trifluoro(organo)borates

L. Navarre, S. Darses, J.-P. Genet, Eur. J. Org. Chem., 2004, 69-73.


Key Words

Borates, Rhodium, Amino esters, Catalysis, Conjugate Addition, Arenes


ID: J48-Y2008-1250