Diastereoselective Photoredox-Catalyzed [3 + 2] Cycloadditions of N-Sulfonyl Cyclopropylamines with Electron-Deficient Olefins.
Diastereoselective Photoredox-Catalyzed [3 + 2] Cycloadditions of N-Sulfonyl Cyclopropylamines with Electron-Deficient Olefins.
复制标题
非对映选择性光氧化还原催化 [3 2] N-磺酰基环丙胺与缺电子烯烃的环加成。
作者：
Dawn H. White;Adam Noble;K. Booker‐Milburn;V. Aggarwal
报道了一种高非对映选择性的可见光诱导的N-磺酰基环丙胺与缺电子烯烃的[3 + 2]环加成反应。该反应通过有机光催化剂氧化磺酰胺氮杂阴离子以产生氮中心自由基来进行。应变诱导的开环和分子间加成到烯烃产生中间体碳中心自由基，其在5-外环化之前被还原成阴离子。这使得能够高度非对映选择性地构建具有合成有用官能团的反式环戊烷。
A highly diastereoselective, visible-light-induced [3 + 2] cycloaddition between N-sulfonyl cyclopropylamines and electron-deficient olefins is reported. The reactions proceed via the oxidation of a sulfonamide aza-anion by an organic photocatalyst to generate a nitrogen-centered radical. Strain-induced ring opening and intermolecular addition to the olefin generate an intermediate carbon-centered radical that is reduced to an anion prior to 5-exo cyclization. This enables a highly diastereoselective construction of trans-cyclopentanes possessing synthetically useful functional groups.
影响因子：
16.6
作者：
Maity, Soumitra;Zhu, Mingzhao;Shinabery, Ryan Spencer;Zheng, Nan
通讯作者：
Zheng, Nan
影响因子：
15
作者：
Speckmeier, Elisabeth;Fischer, Tillmann G.;Zeitler, Kirsten
通讯作者：
Zeitler, Kirsten
影响因子：
23.5
作者：
Staveness, Daryl;Sodano, Taylor M.;Stephenson, Corey R. J.
通讯作者：
Stephenson, Corey R. J.