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

Research output: Journal Publications and ReviewsRGC 21 - Publication in refereed journalpeer-review

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Author(s)

Detail(s)

Original languageEnglish
Pages (from-to)7230-7233
Journal / PublicationOrganic Letters
Volume22
Issue number18
Online published31 Aug 2020
Publication statusPublished - 18 Sept 2020
Externally publishedYes

Abstract

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. © 2020 American Chemical Society.

Citation Format(s)

Iridium-Catalyzed Asymmetric Hydrogenation of α-Fluoro Ketones via a Dynamic Kinetic Resolution Strategy. / Tan, Xuefeng; Zeng, Weijun; Wen, Jialin et al.
In: Organic Letters, Vol. 22, No. 18, 18.09.2020, p. 7230-7233.

Research output: Journal Publications and ReviewsRGC 21 - Publication in refereed journalpeer-review