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Highly enantioselective reduction of ketones in air catalyzed by Rh-based macrocycles
Catalysis Communications ( IF 3.7 ) Pub Date : 2018-10-30 , DOI: 10.1016/j.catcom.2018.10.030
Wen-Jing Zhang , Sun-Hong Ruan , Wei-Yi Shen , Zhe Wang , Dong-Li An , Yan-Yun Li , Jing-Xing Gao

The asymmetric transfer hydrogenation (ATH) of ketones catalyzed by Rh-based macrocycles proceeded smoothly in the presence of air with high catalytic activity and enantioselectivity. Even though the S/C ratio (substrate to catalyst molar ratio) was increased up to 2000:1, the ATH of ketone still afforded 92% isolated yield with 92% ee. Notably, the Rh-based macrocycles could be successfully used to catalyze the ATH of ketones without any need of inert atmosphere, which further highlighted its advantage over those generally air-sensitive transition metal catalysts. The addition of NH4I greatly improved both the catalytic activity and enantioselectivity. On the basis of NMR evidence, we postulate that the NH4I significantly enhanced the coordination between chiral macrocyclic ligands and rhodium center.



中文翻译:

Rh基大环催化的空气中酮的高度对映选择性还原

Rh基大环催化的酮的不对称转移氢化(ATH)在具有高催化活性和对映选择性的空气中平稳进行。即使将S / C比(底物与催化剂的摩尔比)提高到2000:1,酮的ATH仍可提供92%的分离收率和92%的ee。值得注意的是,基于Rh的大环化合物可以成功地用于催化酮的ATH,而无需惰性气氛,这进一步突出了其相对于那些通常对空气敏感的过渡金属催化剂的优势。NH 4 I的添加大大提高了催化活性和对映选择性。根据NMR证据,我们假设NH 4我显着增强了手性大环配体与铑中心之间的配位。

更新日期:2018-10-30
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