Nickel/SKP-Catalyzed Markovnikov Regio- and Enantioselective Hydroamination of Vinylarenes with Hydroxylamines

被引：4

作者：

Wang, Chengdong ^{[1
]}

Wang, Xingheng ^{[2
]}

Wang, Zheng ^{[2
]}

Ding, Kuiling ^{[1
,2
]}

机构：

[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Frontier Sci Ctr Transformat Mol, Shanghai Key Lab Mol Engn Chiral Drugs, Shanghai 200240, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Ctr Excellence Mol Synth, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 35期

基金：

中国国家自然科学基金;

关键词：

ASYMMETRIC-SYNTHESIS; ALKENES; LIGANDS;

D O I：

10.1021/acs.orglett.3c02442

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Ni-catalyzed enantioselective hydroamination of vinylarenes has been developed, affording a wide variety of alpha-branched chiral alkylamines in good yields with exclusive Markovnikov regioselectivity and excellent enantioselectivity. The SKP ligand was found to be crucial to both the reactivity enhancement and enantiocontrol of the reaction. The synthetic utility of the protocol was exemplified in a gram-scale reaction and late-stage modification of medicinally relevant molecules. The deuterium-labeling experiment revealed that the irreversible hydronickelation of vinylarenes is most likely the enantioselectivity-determining step.

引用

页码：6577 / 6581

页数：5

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