Highly Enantioselective Cross-Electrophile Aryl-Alkenylation of Unactivated Alkenes

被引:183
作者
Tian, Zhi-Xiong [1 ]
Qiao, Jin-Bao [1 ]
Xu, Guang-Li [1 ]
Pang, Xiaobo [1 ]
Qi, Liangliang [1 ]
Ma, Wei-Yuan [1 ]
Zhao, Zhen-Zhen [1 ]
Duan, Jicheng [1 ]
Du, Yun-Fei [1 ]
Su, Peifeng [1 ]
Liu, Xue-Yuan [1 ]
Shu, Xing-Zhong [1 ]
机构
[1] Lanzhou Univ, Coll Chem & Chem Engn, SKLAOC, 222 South Tianshui Rd, Lanzhou 730000, Peoples R China
基金
中国国家自然科学基金;
关键词
PALLADIUM-CATALYZED 1,4-DIFUNCTIONALIZATION; COUPLING REACTIONS; REDUCTIVE DICARBOFUNCTIONALIZATION; NICKEL; HALIDES; DIFUNCTIONALIZATION; CONSTRUCTION; CYCLIZATION; ALKYLATION; ALLYLATION;
D O I
10.1021/jacs.9b03863
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Enantioselective cross-electrophile reactions remain a challenging subject in metal catalysis, and with respect to data, studies have mainly focused on stereoconvergent reactions of racemic alkyl electrophiles. Here, we report an enantioselective cross-electrophile aryl-alkenylation reaction of unactivated alkenes. This method provides access to a number of biologically important chiral molecules such as dihydrobenzofurans, indolines, and indanes. The incorporated alkenyl group is suitable for further reactions that can lead to an increase under mild conditions at room temperature, and an easily accessible chiral pyrox ligand is used to afford products with high enantioselectivity. The synthetic utility of this method is demonstrated by enabling the modification of complex molecules such as peptides, indometacin, and steroids.
引用
收藏
页码:7637 / 7643
页数:7
相关论文
共 80 条
[1]  
Attorusso E., 2008, MODERN ALKALOIDS STR
[2]   Enantioselective total syntheses of welwitindolinone A and fischerindoles I and G [J].
Baran, PS ;
Richter, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (44) :15394-15396
[3]   Recent Progress in the Synthesis of 2,3-Dihydrobenzofurans [J].
Bertolini, Ferruccio ;
Pineschi, Mauro .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2009, 41 (05) :385-418
[4]   Enantioselective Michael/Mannich Polycyclization Cascade of Indolyl Enones Catalyzed by Quinine-Derived Primary Amines [J].
Cai, Quan ;
Zheng, Chao ;
Zhang, Jun-Wei ;
You, Shu-Li .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (37) :8665-8669
[5]   Chiral N,NLigands Enabling Palladium-Catalyzed Enantioselective Intramolecular Heck-Matsuda Carbonylation Reactions by Sequential Migratory and CO Insertions [J].
Carmona, Rafaela C. ;
Koster, Otto D. ;
Duarte Correia, Carlos Roque .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (37) :12067-12070
[6]   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
[7]   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
[8]   Transition metal-catalyzed alkyl-alkyl bond formation: Another dimension in cross-coupling chemistry [J].
Choi, Junwon ;
Fu, Gregory C. .
SCIENCE, 2017, 356 (6334)
[9]   Catalytic Enantioselective Cyclization/Cross-Coupling with Alkyl Electrophiles [J].
Cong, Huan ;
Fu, Gregory C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (10) :3788-3791
[10]   Nickel-Catalyzed β,γ-Dicarbofunctionalization of Alkenyl Carbonyl Compounds via Conjunctive Cross-Coupling [J].
Derosa, Joseph ;
Tran, Van T. ;
Boulous, Mark N. ;
Chen, Jason S. ;
Engle, Keary M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (31) :10657-10660