Nickel-Catalyzed Asymmetric C-Alkylation of Nitroalkanes: Synthesis of Enantioenriched β-Nitroamides

被引：29

作者：

Devannah, Vijayarajan ^{[1
]}

Sharma, Rajgopal ^{[1
]}

Watson, Donald A. ^{[1
]}

机构：

[1] Univ Delaware, Dept Chem & Biochem, Newark, DC 19716 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2019年 / 141卷 / 21期

关键词：

CONJUGATE ADDITION; HENRY REACTION; REAGENTS; KINETICS;

D O I：

10.1021/jacs.9b04175

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A general catalytic method for asymmetric C-alkylation of nitroalkanes using nickel catalysis is described. This method enables the formation of highly enantioenriched beta-nitroamides from readily available alpha-bromoamides using mild reaction conditions that are compatible with a wide range of functional groups. When combined with subsequent reactions, this method allows access to highly enantioenriched products with nitrogen bearing fully substituted carbon centers.

引用

页码：8436 / 8440

页数：5

共 46 条

[1]

[Anonymous], 2001, The Nitro Group in Organic Synthesis

[2]

Arend M, 1998, ANGEW CHEM INT EDIT, V37, P1044, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO

[3]

2-E

[4] Synthetic Procedures for the Preparation of Nitroalkanes [J].

Ballini, Roberto ;

Palmieri, Alessandro .

ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (12) :2240-2266

[5] 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

[6] Development of New N,N-Ligands for the Enantioselective Copper(II)-Catalyzed Henry Reaction [J].

Blay, Gonzalo ;

Hernandez-Olmos, Victor ;

Pedro, Jose R. .

SYNLETT, 2011, (09) :1195-1211

[7] KINETICS OF NITROXIDE RADICAL TRAPPING .2. STRUCTURAL EFFECTS [J].

BOWRY, VW ;

INGOLD, KU .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :4992-4996

[8]

BRANCHAUD BP, 1988, TETRAHEDRON LETT, V29, P6545

[9] Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds [J].

Cherney, Alan H. ;

Kadunce, Nathaniel T. ;

Reisman, Sarah E. .

CHEMICAL REVIEWS, 2015, 115 (17) :9587-9652

[10] Transition metal-catalyzed alkyl-alkyl bond formation: Another dimension in cross-coupling chemistry [J].

Choi, Junwon ;

Fu, Gregory C. .

SCIENCE, 2017, 356 (6334)

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