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Synlett 2011(13): 1831-1834  
DOI: 10.1055/s-0030-1260961
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Highly Regioselective and Efficient Synthesis of Aminoepoxides by Ring Closure of Aminohalohydrins Mediated by KF-Celite

Vittorio Pace*a,b, Pilar Hoyosb, José Vicente Sinisterrab,c, Andrés R. Alcántarab, Wolfgang Holzera
a Department of Drug and Natural Product Synthesis, Faculty of Life Sciences, University of Vienna, Althanstr. 14, 1090 Vienna, Austria
b Biotransformations Group, Organic and Pharmaceutical Chemistry Department, Complutense University of Madrid, Plaza Ramón y Cajal s/n, 28040 Madrid, Spain
Fax: +34(913)941822; e-Mail: vpace@farm.ucm.es;
c Industrial Biotransformations Unit, Scientific Park of Madrid, 28760 Tres Cantos, Madrid, Spain
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Publication History

Received 3 March 2011
Publication Date:
21 July 2011 (online)

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Abstract

The regioselective synthesis of several aminoepoxides has been achieved without observing any trace of azetidinols, which are usually reported as the exclusive reaction products when aminohalohydrins are treated with bases. The use of the mild supported base KF-Celite in refluxing acetonitrile is crucial for modulating the excellent regioselectivity observed.

Key words

epoxides - amino alcohols - regioselectivity - ring closure - epoxidation