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Iron‐Promoted Radical Cyclization of β, γ‐Unsaturated Oximes: Dual Role of Iron(III) Nitrate as a Promoter and Nitrooxy Source
Author(s) -
Yu Wei,
Wang PeiLong,
Xu Ke,
Li Hongji
Publication year - 2021
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202100040
Subject(s) - chemistry , dual role , alkyl , nitrate , radical cyclization , dual (grammatical number) , combinatorial chemistry , organic chemistry , medicinal chemistry , art , literature
A method for the radical cyclization of β,γ‐unsaturated oximes to access the isoxazoline backbone has been developed, in which iron(III) nitrate plays a dual role as a promoter and a nitrooxy source. Iron‐promoted cyclization is well tolerated with a series of aryl‐ and alkyl‐substituted β,γ‐unsaturated oximes, which readily affords the desired isoxazolines that can be easily transformed into useful compounds. Mechanistic experiments support that a radical pathway may be involved in the cyclization of β,γ‐unsaturated oximes.