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Synfacts 2011(10): 1051-1051
DOI: 10.1055/s-0030-1261104
DOI: 10.1055/s-0030-1261104
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of 2-Aminoepoxides from Aminohalohydrins Using KF on Celite
V. Pace*, P. Hoyos, J. V. Sinisterra, A. R. Alcántara, W. Holzer
University of Vienna, Austria; Complutense University of Madrid and Industrial Biotransformations Unit, Scientific Park of Madrid, Spain
Further Information
Publication History
Publication Date:
20 September 2011 (online)
Significance
Reported is the synthesis of 2-aminoepoxides from aminohalohydrin-type compounds through the use of potassium fluoride supported on celite to selectively activate the alcohol over the secondary amine. This strategy was successful, producing high yields of epoxides with no azetidine formation being observed. The use of potassium fluoride on celite has been previously reported by the same group as a reagent to allow the monoallylation of anilines (V. Pace et al. Org. Lett. 2007, 9, 2661). Other bases, including unsupported potassium fluoride, were tested but only potassium fluoride supported on celite provided a regioselective protocol.