Highly Diastereoselective Synthesis of γ-Lactams Enabled by Photoinduced Deaminative [3 + 2] Annulation Reaction

作者：Chengcheng Shi, Lin Guo, Han Gao, Mengqi Luo, Chao Yang, Wujiong Xia · 发表于：Organic Letters · 年份：2022 · DOI：10.1021/acs.orglett.2c01565 · 被引用次数：39 · 研究领域：Radical Photochemical Reactions、Catalytic C–H Functionalization Methods、Oxidative Organic Chemistry Reactions

The photoinitiated deaminative [3 + 2] annulation reaction of N -aminopyridinium salts with alkenes for the synthesis of functionalized γ-lactams is described. This transformation shows good functional group tolerance as well as excellent diastereoselectivity. Preliminary studies suggest that the employed N -aminopyridinium salts generate the key amidyl radical intermediates through N–N bond cleavage via a photoinduced single-electron transfer (SET) process. The amidyl radical species would add to the double bond of alkenes, followed by a radical-mediated annulation process, to afford the desired γ-lactams.