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Iminyl radical-promoted imino sulfonylation, imino cyanogenation and imino thiocyanation of γ,δ-unsaturated oxime esters: synthesis of versatile functionalized pyrrolines

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Abstract

An efficient approach for the cascade radical cyclization/functionalization of γ,δ-unsaturated oxime esters was developed, which introduced useful functional groups (–SO2R, –CN, –SCN) into pyrrolines. Control experiments were conducted and a mechanism involving iminyl radical intermediates, which was initiated by Cu(I) species, was proposed.

Graphical abstract: Iminyl radical-promoted imino sulfonylation, imino cyanogenation and imino thiocyanation of γ,δ-unsaturated oxime esters: synthesis of versatile functionalized pyrrolines

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Publication details

The article was received on 25 Mar 2019, accepted on 02 May 2019 and first published on 06 May 2019


Article type: Research Article
DOI: 10.1039/C9QO00421A
Org. Chem. Front., 2019, Advance Article

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    Iminyl radical-promoted imino sulfonylation, imino cyanogenation and imino thiocyanation of γ,δ-unsaturated oxime esters: synthesis of versatile functionalized pyrrolines

    Y. Wang, J. Ding, J. Zhao, W. Sun, C. Lian, C. Chen and B. Zhu, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00421A

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