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

Vittorio Pace*, Pilar Hoyos, José Vicente Sinisterra, Andrés R. Alcántara, Wolfgang Holzer

*iotransformations Group, Organic and Pharmaceutical Chemistry Department, Complutense University of Madrid, Plaza Ramón y Cajal s/n, 28040 Madrid, Spain, Email:

V. Pace, P. Hoyos, J. V. Sinisterra, A. R. Alcántara, W. Holzer, Synlett, 2011, 1831-1834.

DOI: 10.1055/s-0030-1260961


The regioselective synthesis of several aminoepoxides has been achieved without observing any trace of azetidinols. The use of the mild supported base KF-Celite in refluxing acetonitrile is crucial for modulating the excellent regioselectivity observed.

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Key Words

epoxides, amino alcohols, regioselectivity, ring closure, epoxidation

ID: J60-Y2011-2180