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Synfacts 2009(7): 0779-0779  
DOI: 10.1055/s-0029-1217262
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Copper-Promoted Intramolecular Aminooxygenation of Alkenes

Contributor(s): Paul Knochel, Andreas J. Wagner
M. C. Paderes, S. R. Chemler*
The State University of New York at Buffalo, USA
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Publication History

Publication Date:
22 June 2009 (online)

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Significance

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.