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

被引：16

作者：

Tan, Xuefeng ^{[1
,2
]}

Zeng, Weijun ^{[1
,2
]}

Wen, Jialin ^{[1
,2
,3
]}

Zhang, Xumu ^{[1
,2
]}

机构：

[1] Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen Key Lab Small Mol Drug Discovery & Synth, Shenzhen 518055, Guangdong, Peoples R China

[2] Southern Univ Sci & Technol, Dept Chem, Shenzhen Key Lab Small Mol Drug Discovery & Synth, Shenzhen 518055, Guangdong, Peoples R China

[3] Southern Univ Sci & Technol, Acad Adv Interdisciplinary Studies, Shenzhen 518055, Guangdong, Peoples R China

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 18期

基金：

中国国家自然科学基金;

关键词：

DOT-M+ INTERACTION; CHIRAL AUXILIARY; METAL-COMPLEXES; MECHANISM; ALKYLATION; LIGANDS;

D O I：

10.1021/acs.orglett.0c02565

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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

引用

页码：7230 / 7233

页数：4

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