Enantioselective Alkylation of Amino Acid Derivatives with Unactivated Olefins via C-N Bond Cleavage

被引:0
作者
Cai, Yue-Ming [1 ]
Shang, Ming [1 ]
机构
[1] Shanghai Jiao Tong Univ, Frontiers Sci Ctr Transformat Mol, Sch Chem & Chem Engn, Shanghai 200240, Peoples R China
基金
中国国家自然科学基金;
关键词
deaminative alkylation; enantioselective; chiral bis(oxazoline) ligands; alpha-amino acid; sp(3) cross-coupling; NICKEL-CATALYZED BORYLATION; BENZYLIC AMMONIUM-SALTS; CROSS-COUPLINGS; H FUNCTIONALIZATION; REDUCTIVE ARYLATION; NATURAL-PRODUCTS; BORONIC ACIDS; REMOTE; LIGANDS; ARYL;
D O I
10.1055/s-0042-1752337
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We reported a nickel-catalyzed enantioconvergent deaminative alkylation of a-amino acid derivatives with unactivated olefins, providing an efficient and convenient access to a range of a-enantioenriched amides. This method represents the first example of enantioselective deaminative functionalization with racemic amine precursors and features in mild conditions and broad substrate scope. New sterically encumbered bis(oxazoline) ligand was developed to improve both reactivity and enantioselectivity, which is key to the success of this reaction.
引用
收藏
页码:875 / 881
页数:7
相关论文
共 74 条
[1]  
Albericio F, 2012, FUTURE MED CHEM, V4, P1527, DOI [10.4155/FMC.12.94, 10.4155/fmc.12.94]
[2]   Harnessing Alkyl Amines as Electrophiles for Nickel-Catalyzed Cross Couplings via C-N Bond Activation [J].
Basch, Corey H. ;
Liao, Jennie ;
Xu, Jianyu ;
Piane, Jacob J. ;
Watson, Mary P. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (15) :5313-5316
[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]   Enantioselective C(sp3)-C(sp3) cross-coupling of non-activated alkyl electrophiles via nickel hydride catalysis [J].
Bera, Srikrishna ;
Mao, Runze ;
Hu, Xile .
NATURE CHEMISTRY, 2021, 13 (03) :270-+
[5]   Nickel-Catalyzed Regioselective Hydroalkylation and Hydroarylation of Alkenyl Boronic Esters [J].
Bera, Srikrishna ;
Hu, Xile .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (39) :13854-13859
[6]   THE CHIRAL POOL AS A SOURCE OF ENANTIOSELECTIVE CATALYSTS AND AUXILIARIES [J].
BLASER, HU .
CHEMICAL REVIEWS, 1992, 92 (05) :935-952
[7]  
Bruckner H., 2011, D-Amino Acids in Chemistry, Life Sciences, and Biotechnology
[8]   Nickel-Catalyzed Multicomponent Coupling: Synthesis of α-Chiral Ketones by Reductive Hydrocarbonylation of Alkenes [J].
Chen, Jian ;
Zhu, Shaolin .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (35) :14089-14096
[9]   Alkyl halides as both hydride and alkyl sources in catalytic regioselective reductive olefin hydroalkylation [J].
Chen, Xianxiao ;
Rao, Weidong ;
Yang, Tao ;
Koh, Ming Joo .
NATURE COMMUNICATIONS, 2020, 11 (01)
[10]   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