The Ir-Catalyzed Asymmetric Hydrogenation of α-Halogenated Ketones Utilizing Cinchona-Alkaloid-Derived NNP Ligand to Produce (R)- and (S)-Halohydrins

被引：7

作者：

Chen, Qian ^{[1
,2
]}

Sun, Hao ^{[1
,2
]}

Li, Linlin ^{[1
,2
]}

Tian, Jie ^{[1
,2
]}

Xu, Qian ^{[1
,2
]}

Ma, Nana ^{[1
,2
]}

Li, Li ^{[1
,2
]}

Zhang, Lin ^{[1
,2
]}

Li, Chun ^{[1
,2
]}

机构：

[1] Guizhou Med Univ, State Key Lab Funct & Applicat Med Plants, Guiyang 550004, Guizhou, Peoples R China

[2] Guizhou Med Univ, Sch Pharmaceut Sci, Guiyang 550004, Guizhou, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 23期

基金：

中国国家自然科学基金;

关键词：

ENANTIOSELECTIVE SYNTHESIS; CHLOROMETHYL KETONES; REDUCTION; ACCESS; COMPLEXES; HALOHYDRINS; DENOPAMINE;

D O I：

10.1021/acs.joc.2c02109

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric hydrogenation of alpha-halogenated ketones with iridium catalyst was developed, utilizing easily accessed cinchona-alkaloid-based NNP ligands. Various alpha-chloroacetophenones, heterocyclic thienyl and furanyl substrates, and even bromoketones were completely converted to the desired chiral halohydrins by this protocol. Both (R)-and (S)-chiral halohydrins can be prepared by changing the configurations of the chiral ligand NNP with up to 99.6% ee (enantiomeric excess) and 98.8% ee, respectively. Also, a gram-scale experiment was carried out efficiently.

引用

页码：15986 / 15997

页数：12

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