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School of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan
; Fax: +81-76-234-4439
Chem. Commun., 2013,49, 2198-2200
07 Jan 2013,
29 Jan 2013
First published online
30 Jan 2013
A method for direct functionalization of three positions including an unactivated C–H bond of aliphatic alkenes using tert-butyl nitrite and molecular oxygen to give γ-lactols has been developed. The present reaction proceeds through a sequence of radical processes involving oxynitration followed by aerobic oxidation of an sp3 C–H bond. This multifunctionalization reaction requires neither metallic reagents nor photolysis and proceeds under mild conditions.
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