Iron-Catalyzed Aminohydroxylation of Olefins

摘要

The osmium-catalyzed Sharpless aminohydroxylation1,2 is anpowerful method for the rapid transformation of alkenes into 1,2-naminoalcohols.3 Because of the cost and toxicity of osmium salts,nhowever, a variety of alternate methods for olefin oxyaminationnthat utilize palladium4 and copper5 catalysts have been developed.nWe previously reported that N-sulfonyl oxaziridines (“Davis’noxaziridines”)6 react with olefins in the presence of copper(II)ncatalysts to afford 1,3-oxazolidines.7 In this communication, wenreport that iron salts8 are also effective catalysts for oxaziridinemediatednoxyamination but provide the opposite regiomeric outcome.nThus, the appropriate choice of inexpensive, nontoxic, firstrowntransition metal in this transformation enables complementarynaccess to 1,2-aminoalcohols in either regioisomeric form.