Issue 13, 2019

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
25 Mar 2019
Accepted
02 May 2019
First published
06 May 2019

Org. Chem. Front., 2019,6, 2240-2244

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, 6, 2240 DOI: 10.1039/C9QO00421A

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