Cobalt-Catalyzed Enantioconvergent Hydrogenation of Minimally Functionalized Isomeric Olefins,Journal of the American Chemical Society

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Cobalt-Catalyzed Enantioconvergent Hydrogenation of Minimally Functionalized Isomeric Olefins
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2022-09-15 , DOI: 10.1021/jacs.2c08525
Peng Lu ₁ , Hongliang Wang _{1,

2} , Yihui Mao ₁ , Xin Hong _{1,

3,

4,

5} , Zhan Lu _{1,

6}

Affiliation

Investigation on asymmetric hydrogenation of olefins is of great importance in both pharmaceutical molecule synthesis and chemical industry due to the high demand for enantiopure compounds. The established methods often require geometrically pure olefins. The enantioconvergent reaction provided the possibility to access a single stereoisomer via hydrogenation of E/Z-olefin mixtures; however, a polar functional group next to the carbon–carbon double bond was usually necessary. Here, we reported a cobalt-catalyzed enantioconvergent hydrogenation of readily available minimally functionalized E/Z-olefin mixtures. This strategy shows good functional group tolerance and provides an alternative means to enantioconvergent transformation. The preliminary mechanistic studies indicated that cobalt-catalyzed isomerization was the key to achieve the convergent transformation.

中文翻译：

钴催化的最小官能化异构烯烃的对映收敛加氢

由于对映体纯化合物的高需求，烯烃不对称氢化的研究在药物分子合成和化学工业中都具有重要意义。已建立的方法通常需要几何纯烯烃。对映收敛反应提供了通过氢化E / Z -烯烃混合物获得单一立体异构体的可能性；然而，通常需要在碳-碳双键旁边的极性官能团。在这里，我们报道了一种钴催化的对映收敛氢化容易获得的最小官能化E / Z-烯烃混合物。该策略显示出良好的官能团耐受性，并为对映收敛转化提供了一种替代方法。初步机理研究表明，钴催化异构化是实现收敛转化的关键。

更新日期：2022-09-15

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