Iminoxyl Radical-Promoted Dichotomous Cyclizations: Efficient Oxyoximation and Aminooximation of Alkenes

A novel iminoxyl radical-involved metal-free approach to vicinal oxyoximation and aminooximation of unactivated alkenes is developed. This method utilizes the dichotomous reactivity of the iminoxyl radical to furnish a general difunctionalization on alkenes using simple tert-butyl nitrite (TBN) as t...

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Bibliographic Details
Published in:Organic letters 2014-09, Vol.16 (17), p.4650-4653
Main Authors: Peng, Xie-Xue, Deng, Yun-Jing, Yang, Xiu-Long, Zhang, Lin, Yu, Wei, Han, Bing
Format: Article
Language:English
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Summary:A novel iminoxyl radical-involved metal-free approach to vicinal oxyoximation and aminooximation of unactivated alkenes is developed. This method utilizes the dichotomous reactivity of the iminoxyl radical to furnish a general difunctionalization on alkenes using simple tert-butyl nitrite (TBN) as the iminoxyl radical initiator as well the carbon radical trap. By using this protocol, oxime featured 4,5-dihydroisoxazoles and cyclic nitrones were facilely prepared from β,γ- and γ,δ-unsaturated ketoximes, respectively.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol502258n