Radical Enamination of Vinyl Azides: Direct Synthesis of N-Unprotected Enamines

Yongquan Ning; Xue-Feng Zhao; Yan-Bo Wu; Xihe Bi

doi:10.1021/acs.orglett.7b03204

Radical Enamination of Vinyl Azides: Direct Synthesis of N-Unprotected Enamines

Org Lett. 2017 Nov 17;19(22):6240-6243. doi: 10.1021/acs.orglett.7b03204. Epub 2017 Nov 1.

Authors

Yongquan Ning¹, Xue-Feng Zhao², Yan-Bo Wu², Xihe Bi^{1

3}

Affiliations

¹ Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University , Changchun 130024, China.
² Key Laboratory of Materials for Energy Conversion and Storage of Shanxi Province, Institute of Molecular Science, Shanxi University , Taiyuan 030006, China.
³ State Key Laboratory of Elemento-Organic Chemistry, Nankai University , Tianjin 300071, China.

PMID: 29090931
DOI: 10.1021/acs.orglett.7b03204

Abstract

An electron-withdrawing-group-generable radical-induced enamination of vinyl azides is reported, which results in a variety of β-functionalized N-unprotected enamines in a stereoselective manner. A plausible mechanism involving an unusual 1,3-H transfer of in situ generated iminyl radical intermediate was proposed on the basis of experimental results and DFT calculations.

Publication types

Research Support, Non-U.S. Gov't