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 (free Supporting Information)

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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

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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.

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Key Words

β-amino alcohols, aziridines, microwave synthesis

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ID: J54-Y2006-2350