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Iridium-Catalyzed Asymmetric Hydrogenation of α-Fluoro Ketones via a Dynamic Kinetic Resolution Strategy

Xuefeng Tan, Weijun Zeng, Jialin Wen* and Xumu Zhang*

*Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong 518055, China, Email: wenjlsustech.edu.cn, zhangxmsustech.edu.cn

X. Tan, W. Zeng, J. Wen, X. Zhang, Org. Lett., 2020, 22, 7230-7233.

DOI: 10.1021/acs.orglett.0c02565


Abstract

An iridium-catalyzed hydrogenation of α-fluoro ketones provides β-fluoro alcohols with good enantiomeric and diastereomeric selectivities using a strategy of dynamic kinetic resolution. A C-FNa charge-dipole interaction in the transition state of hydride transfer is responsible for the diastereomeric control.

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Key Words

fluorohydrins, reduction of carbonyl compounds, hydrogen


ID: J54-Y2020