Highly Enantioselective Synthesis of β-Amino Alcohols
Thomas-Xavier Métro, Jérôme Appenzeller, Domingo Gomez Pardo* and Janine Cossy*
*Laboratoire de Chimie Organique, associé au CNRS, Ecole Supérieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI), 10 rue Vauquelin, 75231 Paris Cedex 05, France, Email: domingo.gomez-pardoespci.fr, janine.cossyespci.fr
T.-X. Métro, J. Appenzeller, D. G. Pardo, J. Cossy, Org. Lett., 2006, 8, 3509-3512.
DOI: 10.1021/ol061133d
Abstract
N,N-Dialkyl-β-amino alcohols derived from α-amino acids can be rearranged enantiospecifically by using TFAA/Et3N/NaOH to give 1,2-amino alcohols.
see article for more examples
proposed mechanism
Highly Enantioselective Synthesis of β-Amino Alcohols: A Catalytic Version
T.-X. Métro, D. G. Pardo, J. Cossy, J. Org. Chem., 2007, 72, 6556-6561.
Key Words
β-amino alcohols, aziridines, microwave synthesis
ID: J54-Y2006-2350