Copper(II)-mediated aminohydroxylation of olefins with N-sulfonyl oxaziridines

ORGN 486

David J. Michaelis, vidmichaelis@chem.wisc.edu, Tehshik P. Yoon, tyoon@chem.wisc.edu, and Christopher J. Shaffer. Department of Chemistry, University of Wisconsin-Madison, 1101 University Ave, Madison, WI 53706
Our lab has recently discovered that N-sulfonyloxaziridines (Davis' oxaziridines) react with olefins in the presence of copper(II) catalysts to produce formal aminohydroxylation products with high regioselectivity. This new reaction represents the first general method for transfer of both the oxygen and nitrogen atoms of an oxaziridine to an organic substrate. While the transformation gives the best results with styrenic olefins, electron-rich olefins such as vinyl ethers, dienes, and allylsilanes and unactivated aliphatic olefins also react to give the aminohydroxylation product. This poster will describe the reaction scope including activated and unactivated olefins and progress towards the asymmetric aminohydroxylation of olefins.