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
J. Am. Chem. Soc., 2007, 129 (18), pp 5830–5831
DOI: 10.1021/ja070519w
Publication Date (Web): April 12, 2007
Copyright © 2007 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, jantilla@cas.usf.edu

Abstract

Abstract Image

A new method for the chiral phosphoric acid-catalyzed reduction of α-imino esters using Hantzsch ester is described. A series of 11 α-imino esters were evaluated, and it was shown that imino substrates derived from substituted aryl and alkyl keto esters could be reduced to the corresponding α-amino ester in excellent yield and in enantiomeric excesses from 94 to 99%. Catalyst loading was 5 mol % in each case, and the reactions were run with toluene as the solvent.

View: Full Text HTML | Hi-Res PDF

Tools

History

  • Published In Issue May 09, 2007
  • Received January 23, 2007

Recommend & Share

Related Content

Other ACS content by these authors: