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自由基烯基化叠氮化物:N-未保护烯胺的直接合成。

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

机构信息

Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University , Changchun 130024, China.

Key Laboratory of Materials for Energy Conversion and Storage of Shanxi Province, Institute of Molecular Science, Shanxi University , Taiyuan 030006, China.

出版信息

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

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.

摘要

报道了一种可生成吸电子基团的自由基诱导的乙烯基叠氮化物的烯胺化反应,该反应以立体选择性的方式得到了各种β-官能化的 N-未保护的烯胺。基于实验结果和 DFT 计算,提出了一个涉及原位生成的亚胺基自由基中间体的不寻常的 1,3-H 转移的可能机制。

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