Cobalt-Catalyzed Regio- and Enantioselective Allylic Amination

被引:94
作者
Ghorai, Samir [1 ]
Chirke, Sahadev Shrihari [1 ]
Xu, Wen-Bin [1 ]
Chen, Jia-Feng [1 ]
Li, Changkun [1 ,2 ]
机构
[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai Key Lab Mol Engn Chiral Drugs, 800 Dongchuan Rd, Shanghai 200240, Peoples R China
[2] Beijing Natl Lab Mol Sci, Beijing 100871, Peoples R China
基金
中国国家自然科学基金;
关键词
ALLYLATION; LIGANDS; HYDROGENATION; REDUCTION; COMPLEXES; ENANTIO;
D O I
10.1021/jacs.9b06035
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first earth-abundant cobalt-catalyzed highly branched- and enantioselective allylic amination of racemic branched allylic carbonates bearing alkyl groups with both aromatic and aliphatic amines has been developed. The process allows rapid access of allylic amines in high yields with exclusively branched selectivity and excellent enantioselectivities (normally 99% ee) under mild reaction conditions.
引用
收藏
页码:11430 / 11434
页数:5
相关论文
共 45 条
[1]   First-Row Transition Metal (De)Hydrogenation Catalysis Based On Functional Pincer Ligands [J].
Alig, Lukas ;
Fritz, Maximilian ;
Schneider, Sven .
CHEMICAL REVIEWS, 2019, 119 (04) :2681-2751
[2]   Green Chemistry: Principles and Practice [J].
Anastas, Paul ;
Eghbali, Nicolas .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (01) :301-312
[3]   Rhodium-Catalyzed Sequential Allylic Amination and Olefin Hydroacylation Reactions: Enantioselective Synthesis of Seven-Membered Nitrogen Heterocycles [J].
Arnold, Jeffrey S. ;
Mwenda, Edward T. ;
Nguyen, Hien M. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (14) :3688-3692
[4]   Rhodium-catalyzed regio- and enantioselective amination of racemic secondary allylic trichloroacetimidates with N-methyl anilines [J].
Arnold, Jeffrey S. ;
Cizio, Gregory T. ;
Heitz, Drew R. ;
Nguyen, Hien M. .
CHEMICAL COMMUNICATIONS, 2012, 48 (94) :11531-11533
[5]   Rhodium-Catalyzed Dynamic Kinetic Asymmetric Transformations of Racemic Tertiary Allylic Trichloroacetimidates with Anilines [J].
Arnold, Jeffrey S. ;
Nguyen, Hien M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (20) :8380-8383
[6]   Allylic Substitutions Catalyzed by Miscellaneous Metals [J].
Begouin, Jeanne-Marie ;
Klein, Johannes E. M. N. ;
Weickmann, Daniel ;
Plietker, Bernd .
TRANSITION METAL CATALYZED ENANTIOSELECTIVE ALLYLIC SUBSTITUTION IN ORGANIC SYNTHESIS, 2012, 38 :269-320
[7]   COBALT(II) CATALYZED ALLYLATION OF 1,3-DICARBONYL COMPOUNDS WITH ALLYL ACETATES [J].
BHATIA, B ;
REDDY, MM ;
IQBAL, J .
TETRAHEDRON LETTERS, 1993, 34 (39) :6301-6304
[8]   Nickel and Iron Pincer Complexes as Catalysts for the Reduction of Carbonyl Compounds [J].
Chakraborty, Sumit ;
Bhattacharya, Papri ;
Dai, Huiguang ;
Guan, Hairong .
ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (07) :1995-2003
[9]   Rhodium-Catalyzed Enantioselective Hydroamination of Alkynes with Indolines [J].
Chen, Qing-An ;
Chen, Zhiwei ;
Dong, Vy M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (26) :8392-8395
[10]   Iridium-Catalyzed Asymmetric Allylic Substitution Reactions [J].
Cheng, Qiang ;
Tu, Hang-Fei ;
Zheng, Chao ;
Qu, Jian-Ping ;
Helmchen, Guenter ;
You, Shu-Li .
CHEMICAL REVIEWS, 2019, 119 (03) :1855-1969