Ni-Catalyzed Asymmetric Reductive Alkenylation of α-Chlorosulfones with Vinyl Bromides

被引:12
作者
Geng, Jingjing [1 ]
Sun, Deli [1 ]
Song, Yanhong [1 ]
Tong, Weiqi [1 ]
Wu, Fan [2 ,3 ]
机构
[1] Shanghai Univ, Ctr Supramol Chem & Catalysis, Dept Chem, Shanghai 200444, Peoples R China
[2] Ningbo Univ, Inst Drug Discovery Technol, Ningbo 315211, Zhejiang, Peoples R China
[3] Ningbo Univ, Qian Xuesen Collaborat Res Ctr Astrochem & Space, Ningbo 315211, Zhejiang, Peoples R China
基金
中国国家自然科学基金;
关键词
ANTIBACTERIAL; EPOXIDES; SULFONES; DESIGN; DRUGS; ACIDS;
D O I
10.1021/acs.orglett.2c00217
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A nickel-catalyzed enantioconvergent reductive cross-coupling of alpha-chlorosulfones with vinyl bromides is described here. This strategy enables the enantioselective construction of chiral allylic sulfones from simple alpha-chlorosulfones and vinyl bromides. The mild reaction conditions lead to excellent functional group compatibility, as evidenced by the broad substrate scope and tolerance of complex bioactive molecules. Our preliminary mechanistic study suggests that this enantioselective vinylation process operates through a radical intermediate.
引用
收藏
页码:1807 / 1811
页数:5
相关论文
共 40 条
[1]   Regio- and Enantioselective Preparation of Chiral Allylic Sulfones Featuring Elusive Quaternary Stereocenters [J].
Cai, Aijie ;
Kleij, Arjan W. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (42) :14944-14949
[2]   Sulfonyl Group-Containing Compounds in the Design of Potential Drugs for the Treatment of Diabetes and Its Complications [J].
Chen, X. ;
Hussain, S. ;
Parveen, S. ;
Zhang, S. ;
Yang, Y. ;
Zhu, C. .
CURRENT MEDICINAL CHEMISTRY, 2012, 19 (21) :3578-3604
[3]   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
[4]   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
[5]   Transition metal-catalyzed alkyl-alkyl bond formation: Another dimension in cross-coupling chemistry [J].
Choi, Junwon ;
Fu, Gregory C. .
SCIENCE, 2017, 356 (6334)
[6]   Stereoconvergent Arylations and Alkenylations of Unactivated Alkyl Electrophiles: Catalytic Enantioselective Synthesis of Secondary Sulfonamides and Sulfones [J].
Choi, Junwon ;
Martin-Gago, Pablo ;
Fu, Gregory C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (34) :12161-12165
[7]   Stereocontrolled synthesis of cyclopropanol amino acids from allylic sulfones:: Conformationally restricted building blocks [J].
Díez, D ;
Garcia, P ;
Marcos, IS ;
Garrido, NM ;
Basabe, P ;
Broughton, HB ;
Urones, JG .
ORGANIC LETTERS, 2003, 5 (20) :3687-3690
[8]   Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry [J].
Feng, Minghao ;
Tang, Bingqing ;
Liang, Steven H. ;
Jiang, Xuefeng .
CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2016, 16 (11) :1200-1216
[9]   Transition-Metal Catalysis of Nucleophilic Substitution Reactions: A Radical Alternative to SN1 and SN2 Processes [J].
Fu, Gregory C. .
ACS CENTRAL SCIENCE, 2017, 3 (07) :692-700
[10]   Highly Regio- and Diastereoselective Anionic [3+2] Cycloaddition under Phase Transfer Catalytic Conditions [J].
Gembus, Vincent ;
Postikova, Svetlana ;
Levacher, Vincent ;
Briere, Jean-Francois .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (10) :4194-4199