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Stereoselective radical C–H alkylation with acceptor/acceptor-substituted diazo reagents via Co(ii)-based metalloradical catalysis

机译:通过基于Co(ii)的金属铁催化与受体/受体取代的重氮试剂进行立体选择性自由基C–H烷基化

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摘要

Co(ii)-based metalloradical catalysis has, for the first time, been successfully applied for asymmetric intramolecular C–H alkylation of acceptor/acceptor-substituted diazo reagents. Through the design and synthesis of a new D 2-symmetric chiral amidoporphyrin as the supporting ligand, the Co(ii)-based metalloradical system, which operates at room temperature, is capable of 1,5-C–H alkylation of α-methoxycarbonyl-α-diazosulfones with a broad range of electronic properties, providing the 5-membered sulfolane derivatives in high yields with excellent diastereoselectivities and enantioselectivities. In addition to complete chemoselectivity toward allylic and allenic C–H bonds, the Co(ii)-based metalloradical catalysis for asymmetric C–H alkylation features a remarkable degree of functional group tolerance.
机译:基于Co(ii)的金属铁催化首次成功地用于受体/受体取代的重氮试剂的不对称分子C–H烷基化反应。通过设计和合成新的D 2-对称手性氨基卟啉作为支撑配体,基于Co(ii)的金属铁体系在室温下运行,能够将α-甲氧基羰基进行1,5-C–H烷基化-α-重氮砜具有广泛的电子特性,可高收率地提供5元环丁砜衍生物,具有出色的非对映选择性和对映选择性。除了对烯丙基和烯丙基CH键具有完全的化学选择性外,基于Co(ii)的不对称CH烷基化的金属催化也具有显着的官能团耐受性。

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