Organic Chemistry Portal

Abstracts

Search:

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

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

DOI: 10.1021/ja070519w (free Supporting Information)


Abstract

α-Imino esters derived from aryl and alkyl keto esters could be reduced to the corresponding α-amino esters in excellent yields and in high enantiomeric excesses using 5 mol-% of a chiral phosphoric acid as catalyst, Hantzsch ester as hydride donor, and toluene as solvent.

see article for more examples



Highly Enantioselective Hydrogenation of Enamides Catalyzed by Chiral Phosphoric Acids

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


Key Words

reduction of imines, reductive amination, α-amino esters, organocatalysis, Hantzsch ester


ID: J48-Y2007-1540