Iridium-Catalyzed Asymmetric Hydrogenation of α-Fluoro Ketones via a Dynamic Kinetic Resolution Strategy.,Organic Letters

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Iridium-Catalyzed Asymmetric Hydrogenation of α-Fluoro Ketones via a Dynamic Kinetic Resolution Strategy.
Organic Letters ( IF 4.9 ) Pub Date : 2020-08-31 , DOI: 10.1021/acs.orglett.0c02565
Xuefeng Tan ₁ , Weijun Zeng ₁ , Jialin Wen _{1,

2} , Xumu Zhang ₁

Affiliation

The discrimination of a fluorine atom from a hydrogen atom has been challenging in asymmetric catalysis. We herein report iridium-catalyzed hydrogenation of α-fluoro ketones using a strategy of dynamic kinetic resolution. Both enantiomeric and diastereomeric selectivities were satisfactory in the preparation of β-fluoro alcohols. The DFT calculation revealed a C–F···Na charge–dipole interaction in the transition state of hydride transfer. This noncovalent interaction would be responsible for the diastereomeric control.

中文翻译：

通过动态动力学拆分策略，铱催化α-氟代酮的不对称加氢。

在不对称催化中，将氟原子与氢原子区分开是具有挑战性的。我们在此报告使用动态动力学拆分策略的铱催化的α-氟代酮氢化。在制备β-氟代醇中，对映异构体和非对映异构体的选择性均令人满意。DFT计算表明，在氢化物转移的过渡态中存在CF-·Na电荷-偶极相互作用。这种非共价相互作用将负责非对映异构体的控制。

更新日期：2020-09-20

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