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
Albicker, Martin R.
Cramer, Nicolai
[J]. 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
Anas, Saithalavi
Cordi, Alex
Kagan, Henri B.
[J]. 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
BISHOP, MJ
MCNUTT, RW
[J]. 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
Boebel, Timothy A.
Hartwig, John F.
[J]. TETRAHEDRON, 2008, 64 (29) : 6824 - 6830
[7] A room-temperature protocol for the rhodium(I)-catalyzed addition of arylboron compounds to sulfinimines
Bolshan, Y
Batey, RA
[J]. 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
Cai, Guixin
Fu, Ye
Li, Yizhou
Wan, Xiaobing
Shi, Zhangjie
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (24) : 7666 - 7673
[9] Palladium(II)-Catalyzed Highly Enantioselective C-H Arylation of Cyclopropylmethylamines
Chan, Kelvin S. L.
Fu, Hai-Yan
Yu, Jin-Quan
[J]. 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 →