Nickel-Catalyzed Enantioselective Reductive Cross-Coupling of Styrenyl Aziridines

被引：234

作者：

Woods, Brian P. ^{[1
]}

Orlandi, Manuel ^{[2
]}

Huang, Chung-Yang ^{[1
]}

Sigman, Matthew S. ^{[2
]}

Doylet, Abigail G. ^{[1
]}

机构：

[1] Princeton Univ, Dept Chem, Princeton, NJ 08544 USA

[2] Univ Utah, Dept Chem, 315 S 1400 E, Salt Lake City, UT 84112 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2017年 / 139卷 / 16期

基金：

美国国家科学基金会;

关键词：

BENZYLIC AMMONIUM-SALTS; ASYMMETRIC AZIRIDINATION; BORONIC ACIDS; ELECTROPHILES; COMPLEXES; LIGANDS; 2-ARYLAZIRIDINES; EPOXIDATION; BORYLATION; ARYLATION;

D O I：

10.1021/jacs.7b03448

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A Ni-catalyzed reductive cross-coupling of styrenyl aziridines with aryl iodides is reported. This reaction proceeds by a stereoconvergent mechanism and is thus amenable to asymmetric catalysis using a chiral bioxazoline ligand for Ni. The process allows facile access to highly enantioenriched 2-arylphenethylamines from racemic aziridines. Multivariate analysis revealed that ligand polarizability, among other features, influences the observed enantioselectivity, shedding light on the success of this emerging ligand class for enantioselective Ni catalysis.

引用

页码：5688 / 5691

页数：4

共 50 条

[1]

Ahneman DT, 2016, CHEM SCI, V7, P7002, DOI [10.1039/c6sc02815b, 10.1039/C6SC02815B]

[2] Dialkyl Ether Formation by Nickel-Catalyzed Cross-Coupling of Acetals and Aryl Iodides [J].

Arendt, Kevin M. ;

Doyle, Abigail G. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (34) :9876-9880

[3] Nickel-Catalyzed Borylation of Benzylic Ammonium Salts: Stereospecific Synthesis of Enantioenriched Benzylic Boronates [J].

Basch, Corey H. ;

Cobb, Kelsey M. ;

Watson, Mary P. .

ORGANIC LETTERS, 2016, 18 (01) :136-139

[4] Advances in Stereoconvergent Catalysis from 2005 to 2015: Transition-Metal-Mediated Stereoablative Reactions, Dynamic Kinetic Resolutions, and Dynamic Kinetic Asymmetric Transformations [J].

Bhat, Vikram ;

Welin, Eric R. ;

Guo, Xuelei ;

Stoltz, Brian M. .

CHEMICAL REVIEWS, 2017, 117 (05) :4528-4561

[5] Experimental Binding Energies in Supramolecular Complexes [J].

Biedermann, Frank ;

Schneider, Hans-joerg .

CHEMICAL REVIEWS, 2016, 116 (09) :5216-5300

[6] Mechanism and Selectivity in Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Halides with Alkyl Halides [J].

Biswas, Soumik ;

Weix, Daniel J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (43) :16192-16197

[7] Organic Electron Donors as Powerful Single-Electron Reducing Agents in Organic Synthesis [J].

Broggi, Julie ;

Terme, Thierry ;

Vanelle, Patrice .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (02) :384-413

[8] Palladium-Catalyzed Enantioselective Redox-Relay Heck Arylation of 1,1-Disubstituted Homoallylic Alcohols [J].

Chen, Zhi-Min ;

Hilton, Margaret J. ;

Sigman, Matthew S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (36) :11461-11464

[9] Nickel-Catalyzed Asymmetric Reductive Cross-Coupling Between Vinyl and Benzyl Electrophiles [J].

Cherney, Alan H. ;

Reisman, Sarah E. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (41) :14365-14368

[10] Catalytic Asymmetric Reductive Acyl Cross-Coupling: Synthesis of Enantioenriched Acyclic α,α-Disubstituted Ketones [J].

Cherney, Alan H. ;

Kadunce, Nathaniel T. ;

Reisman, Sarah E. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (20) :7442-7445

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