Intramolecular Radical Aziridination of Allylic Sulfamoyl Azides by Cobalt(II)-Based Metalloradical Catalysis: Effective Construction of Strained Heterobicyclic Structures.
Intramolecular Radical Aziridination of Allylic Sulfamoyl Azides by Cobalt(II)-Based Metalloradical Catalysis: Effective Construction of Strained Heterobicyclic Structures.
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DOI：
10.1002/anie.201605238
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发表时间：
2016-09-12
期刊：
影响因子：
--
通讯作者：
Zhang XP
中科院分区：
文献类型：
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作者：
Jiang H;Lang K;Lu H;Wojtas L;Zhang XP
Co（II）基金属自由基催化剂（MRC）已成功地应用于通过烯丙基氨磺酰叠氮分子内的氮丙啶化反应，以高产率有效地构建了高度紧张的2-磺酰基-1，3-二氮杂双环[3.1.0]-己烷结构。所得到的[3.1.0]-双环氮杂环丙烷证明是用于制备各种各样的1，2-和1，3-二胺衍生物通过选择性开环反应在exo-和endo-的方式，分别通用的配体。作为其应用于靶向合成的示范，金属自由基分子内氮丙啶化反应已被纳入作为有效合成有效的神经激肽1（NK 1）拮抗剂的关键步骤，总收率为60%。
Co(II)-based metalloradical catalysis (MRC) has been successfully applied for effective construction of the highly strained 2-sulfonyl-1,3-diazabicyclo[3.1.0]-hexane structures in high yields through intramolecular radical aziridination of allylic sulfamoyl azides. The resulting [3.1.0]-bicyclic aziridines prove to be versatile synthons for preparation of a diverse range of 1,2- and 1,3-diamine derivatives by selective ring-opening reactions in exo- and endo-fashion, respectively. As a demonstration of its application for target synthesis, the metalloradical intramolecular aziridination reaction has been incorporated as a key step for efficient synthesis of a potent neurokinin 1 (NK1) antagonist in 60% overall yield.