Abstract
The authors report an efficient intramolecular aminooxygenation of protected primary amines bearing a terminal olefin. The suggested mechanism involves the selective syn-aminocupration of the double bond via a chair- or boat-like transition state. The following radical elimination of Cu(I) and recombination of the resulting 2,5-syn-configured pyrrolidinyl radicals with TEMPO affords the corresponding alkoxyl-amines in high diastereoselectivity and excellent yields.
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