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Highly Enantioselective Hydrogenation of Enamides Catalyzed by Chiral Phosphoric Acids

Guilong Li and Jon C. Antilla*

*Department of Chemistry, University of South Florida, 4202 East Fowler Avenue CHE205A, Tampa, Florida 33620, Email: jantillacas.usf.edu

G. Li, J. C. Antilla, Org. Lett., 2009, 11, 1075-1078.

DOI: 10.1021/ol802860u (free Supporting Information)



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Abstract

A highly enantioselective hydrogenation of enamides is catalyzed by a dual chiral-achiral acid system. By employing a substoichiometric amount of a chiral phosphoric acid and acetic acid, low catalyst loadings of the chiral catalyst were sufficient to provide excellent yield and enantioselectivity of the reduction product.

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A Vaulted Biaryl Phosphoric Acid-Catalyzed Reduction of α-Imino Esters: The Highly Enantioselective Preparation of α-Amino Esters

G. Li, Y. Liang, J. C. Antilla, J. Am. Chem. Soc., 2007, 129, 5830-5831.


Key Words

Hydrogenation, Hantzsch ester, Organocatalysis


ID: J54-Y2009-0680