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

Laure Navarre, Sylvain Darses*, Jean-Pierre Genet*

*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:,

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

DOI: 10.1002/ejoc.200300462


Potassium trifluoro(organo)borates, which are highly stable and easily prepared organoboron derivatives, were able to react with various dehydroamino esters to give alanine derivatives in good yields. This reaction, catalyzed by rhodium complexes, tolerates a great variety of amino protecting groups.

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

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

Key Words

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

ID: J24-Y2004-190