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

Xuefeng Tan; Weijun Zeng; Jialin Wen; Xumu Zhang

doi:10.1021/acs.orglett.0c02565

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

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

^*Corresponding author for this work

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

22 Citations (Scopus)

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.

Original language	English
Pages (from-to)	7230-7233
Journal	Organic Letters
Volume	22
Issue number	18
Online published	31 Aug 2020
DOIs	https://doi.org/10.1021/acs.orglett.0c02565
Publication status	Published - 18 Sept 2020
Externally published	Yes

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title = "Iridium-Catalyzed Asymmetric Hydrogenation of α-Fluoro Ketones via a Dynamic Kinetic Resolution Strategy",

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. {\textcopyright} 2020 American Chemical Society.",

author = "Xuefeng Tan and Weijun Zeng and Jialin Wen and Xumu Zhang",

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doi = "10.1021/acs.orglett.0c02565",

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T1 - Iridium-Catalyzed Asymmetric Hydrogenation of α-Fluoro Ketones via a Dynamic Kinetic Resolution Strategy

AU - Tan, Xuefeng

AU - Zeng, Weijun

AU - Wen, Jialin

AU - Zhang, Xumu

PY - 2020/9/18

Y1 - 2020/9/18

N2 - 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.

AB - 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.

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UR - https://www.scopus.com/record/pubmetrics.uri?eid=2-s2.0-85091263779&origin=recordpage

U2 - 10.1021/acs.orglett.0c02565

DO - 10.1021/acs.orglett.0c02565

M3 - RGC 21 - Publication in refereed journal

C2 - 32866391

SN - 1523-7060

VL - 22

SP - 7230

EP - 7233

JO - Organic Letters

JF - Organic Letters

IS - 18

ER -

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

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