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Rhodium-Catalyzed Asymmetric Hydrogenation and Transfer Hydrogenation of α-Nitro Ketones
Organic Letters ( IF 4.9 ) Pub Date : 2024-11-13 , DOI: 10.1021/acs.orglett.4c03859
Hao Sun, Liren Xu, Sai Ruan, Virginie Ratovelomanana-Vidal, Gen-Qiang Chen, Xumu Zhang

A catalytic protocol for the enantioselective hydrogenation and transfer hydrogenation of α-nitro ketones was developed, providing a wide range of β-nitro-α-phenylethanols with high yields and excellent enantioselectivities (up to 98% yield and up to >99.9% ee). Compatibility with a wide range of solvents and bases demonstrates the robustness of this reaction. The synthetic potential of the protocol was demonstrated by the high TON experiment as well as the application in the synthesis of key intermediates of mirabegron (S/C = 10,000, 95% yield, 99% ee).

中文翻译:


铑催化的 α-硝基酮的不对称加氢和转移加氢



开发了一种用于 α-硝基酮对映选择性加氢和转移加氢的催化方案,提供了多种 β-硝基-α-苯乙醇,具有高产率和优异的对映选择性(高达 98% 的产率和高达 >99.9% ee)。与多种溶剂和碱的相容性证明了该反应的稳定性。高 TON 实验以及在米拉贝隆关键中间体合成中的应用证明了该方案的合成潜力 (S/C = 10,000,95% 产率,99% ee)。
更新日期:2024-11-14
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