Alkene - and -Oxyamination with Malonoyl Peroxides.

Malonoyl peroxide is an effective reagent for the - or -oxyamination of alkenes. Reaction of and an alkene in the presence of --butyl--tosylcarbamate (R = COBu) leads to the -oxyaminated product in up to 99% yield. Use of -methyl--tosyl carbamate (R = COMe) as the nitrogen nucleophile followed by treatment of the product with trifluoroacetic acid leads to the -oxyaminated product in up to 77% yield. Mechanisms consistent with the observed selectivities are proposed.