Enantioselective ortho-C-H Cross-Coupling of Diarylmethylamines with Organoborons

被引：60

作者：

Laforteza, Brian N. ^{[1
]}

Chan, Kelvin S. L. ^{[1
]}

Yu, Jin-Quan ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 38期

关键词：

amino acid ligands; C-H activation; C-H coupling; enantioselective catalysis; palladium; PALLADIUM-CATALYZED ARYLATION; ASYMMETRIC-SYNTHESIS; FREE-AMINE; BONDS; ACTIVATION; INDOLINES; FUNCTIONALIZATION; IODINATION; ALKYLATION; CETIRIZINE;

D O I：

10.1002/anie.201505204

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The commonly used para-nitrobenzenesulfonyl (nosyl) protecting group is employed to direct the C-H activation of amines for the first time. An enantioselective ortho-C-H cross-coupling between nosyl-protected diarylmethylamines and arylboronic acid pinacol esters has been achieved utilizing chiral mono-N-protected amino acid (MPAA) ligands as a promoter.

引用

页码：11143 / 11146

页数：4

共 53 条

[1]

Albicker M.R., 2009, Angew. Chem. 2009, V121, P9303

[2] Enantioselective Palladium-Catalyzed Direct Arylations at Ambient Temperature: Access to Indanes with Quaternary Stereocenters [J].

Albicker, Martin R. ;

Cramer, Nicolai .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (48) :9139-9142

[3] Enantioselective synthesis of 2-methyl indolines by palladium catalysed asymmetric C(sp3)-H activation/cyclisation [J].

Anas, Saithalavi ;

Cordi, Alex ;

Kagan, Henri B. .

CHEMICAL COMMUNICATIONS, 2011, 47 (41) :11483-11485

[4]

BILSKY EJ, 1995, J PHARMACOL EXP THER, V273, P359

[5] AN EFFICIENT SYNTHESIS OF THE BENZHYDRYLPIPERAZINE DELTA-OPIOID AGONIST (+)-BW373U86 [J].

BISHOP, MJ ;

MCNUTT, RW .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (12) :1311-1314

[6] Conversion of 1,3-disubstituted arenes to chiral α,α-diaryl methylammonium chlorides using arene borylation [J].

Boebel, Timothy A. ;

Hartwig, John F. .

TETRAHEDRON, 2008, 64 (29) :6824-6830

[7] A room-temperature protocol for the rhodium(I)-catalyzed addition of arylboron compounds to sulfinimines [J].

Bolshan, Y ;

Batey, RA .

ORGANIC LETTERS, 2005, 7 (08) :1481-1484

[8] Indirect ortho functionalization of substituted toluenes through ortho olefination of N,N-dimethylbenzylamines tuned by the acidity of reaction conditions [J].

Cai, Guixin ;

Fu, Ye ;

Li, Yizhou ;

Wan, Xiaobing ;

Shi, Zhangjie .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (24) :7666-7673

[9] Palladium(II)-Catalyzed Highly Enantioselective C-H Arylation of Cyclopropylmethylamines [J].

Chan, Kelvin S. L. ;

Fu, Hai-Yan ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (05) :2042-2046

[10]

Chan KSL, 2014, NAT CHEM, V6, P146, DOI [10.1038/NCHEM.1836, 10.1038/nchem.1836]

← 1 2 3 4 5 6 →