Steric Modulation of Chiral Biaryl Diamines via Pd-Catalyzed Directed C-H Arylation

被引：38

作者：

Scarborough, Christopher C. ^{[1
]}

McDonald, Richard I. ^{[1
]}

Hartmann, Caroline ^{[1
]}

Sazama, Graham T. ^{[1
]}

Bergant, Ana ^{[1
]}

Stahl, Shannon S. ^{[1
]}

机构：

[1] Univ Wisconsin, Dept Chem, Madison, WI 53706 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 06期

关键词：

ANILIDE ORTHO-ARYLATION; SCHIFF-BASE COMPLEXES; DIELS-ALDER REACTION; ENANTIOSELECTIVE HYDROAMINATION/CYCLISATION; ASYMMETRIC CATALYSIS; ALKENE AZIRIDINATION; AMIDATE COMPLEXES; COPPER-COMPLEXES; LIGANDS; HYDROGENATION;

D O I：

10.1021/jo802632v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium-catalyzed directed arylation of 2,2'-diacetamidobiaryls with aryl iodides provides efficient access to chiral ortho-substituted biaryl diamines. Aryl iodides with para and meta-substituents are tolerated. Deprotection of the acetyl groups under basic conditions furnishes the free diamines, which should find broad utility in asymmetric catalysis.

引用

页码：2613 / 2615

页数：3

共 50 条

[1] Recent progress in chiral Bronsted acid catalysis [J].

Akiyama, Takahiko ;

Itoh, Junji ;

Fuchibe, Kohei .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (09) :999-1010

[2] Cis-selective asymmetric cyclopropanation of olefins catalyzed by five-coordinate [RuCl(PNNP)]+ complexes [J].

Bachmann, S ;

Furler, M ;

Mezzetti, A .

ORGANOMETALLICS, 2001, 20 (10) :2102-2108

[3] Axially chiral NHC-Pd(II) complexes in the oxidative kinetic resolution of secondary alcohols using molecular oxygen as a terminal oxidant [J].

Chen, Tao ;

Jiang, Jia-Jun ;

Xu, Qin ;

Shi, Min .

ORGANIC LETTERS, 2007, 9 (05) :865-868

[4] Application of phosphinous amide ligands in palladium complex-catalyzed asymmetric allylic alkylation: influence of steric effects on enantioselectivity [J].

Chen, XH ;

Guo, RW ;

Li, YM ;

Chen, G ;

Yeung, CH ;

Chan, ASC .

TETRAHEDRON-ASYMMETRY, 2004, 15 (02) :213-217

[5] Modified BINOL ligands in asymmetric catalysis [J].

Chen, Y ;

Yekta, S ;

Yudin, AK .

CHEMICAL REVIEWS, 2003, 103 (08) :3155-3211

[6]

Chen YX, 2003, CHINESE J CHEM, V21, P66

[7]

Chen YX, 2002, CHINESE J CHEM, V20, P606

[8]

Chen YX, 2001, CHINESE J CHEM, V19, P794

[9] Anilide ortho-arylation by using C-H activation methodology [J].

Daugulis, O ;

Zaitsev, VG .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (26) :4046-4048

[10] Enantioselective aziridination using copper complexes of biaryl Schiff bases [J].

Gillespie, KM ;

Sanders, CJ ;

O'Shaughnessy, P ;

Westmoreland, I ;

Thickitt, CP ;

Scott, P .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (10) :3450-3458

← 1 2 3 4 5 →