Copper-Catalyzed Aerobic Spirocyclization of Biaryl-N-H-imines via 1,4-Aminooxygenation of Benzene Rings

被引：48

作者：

Tnay, Ya Lin ^{[1
]}

Chen, Cheng ^{[1
]}

Chua, Yi Yuan ^{[1
]}

Zhang, Line ^{[1
]}

Chiba, Shunsuke ^{[1
]}

机构：

[1] Nanyang Technol Univ, Div Chem & Biol Chem, Sch Phys & Math Sci, Singapore 637371, Singapore

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 13期

关键词：

OXIDATIVE AMIDATION; AXIAL CHIRALITY; BOND FORMATION; FUNCTIONALIZATIONS; DEAROMATIZATION; DERIVATIVES; ALKYNES; ACCESS; OXYGEN; SCOPE;

D O I：

10.1021/ol301583y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthetic method of azaspirocyclohexadienones has been developed through copper-catalyzed aerobic spirocyclization of biaryl-N-H-imines prepared by the reaction of biarylcarbonitriles and Grignard reagents.

引用

页码：3550 / 3553

页数：4

共 44 条

[1] Pyrroloiminoquinone and related metabolites from marine sponges [J].

Antunes, EM ;

Copp, BR ;

Davies-Coleman, MT ;

Samaai, T .

NATURAL PRODUCT REPORTS, 2005, 22 (01) :62-72

[2] C-H functionalization/C-N bond formation: Copper-catalyzed synthesis of benzimidazoles from amidines [J].

Brasche, Gordon ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) :1932-1934

[3] Novel concepts in directed biaryl synthesis, part 78. The lactone concept: An efficient pathway to axially chiral natural products and useful reagents [J].

Bringmann, G ;

Breuning, M ;

Tasler, S .

SYNTHESIS-STUTTGART, 1999, (04) :525-558

[4] Atroposelective synthesis of axially chiral biaryl compounds [J].

Bringmann, G ;

Mortimer, AJP ;

Keller, PA ;

Gresser, MJ ;

Garner, J ;

Breuning, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (34) :5384-5427

[5] Atroposelective Total Synthesis of Axially Chiral Biaryl Natural Products [J].

Bringmann, Gerhard ;

Gulder, Tanja ;

Gulder, Tobias A. M. ;

Breuning, Matthias .

CHEMICAL REVIEWS, 2011, 111 (02) :563-639

[6] Structure, bioactivities, biosynthetic relationships and chemical synthesis of the spirodioxynaphthalenes [J].

Cai, You-Sheng ;

Guo, Yue-Wei ;

Krohn, Karsten .

NATURAL PRODUCT REPORTS, 2010, 27 (12) :1840-1870

[7] ERYTHRINA AND RELATED ALKALOIDS [J].

CHAWLA, AS ;

JACKSON, AH .

NATURAL PRODUCT REPORTS, 1989, 6 (01) :55-66

[8] Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant [J].

Chen, Xiao ;

Hao, Xue-Shi ;

Goodhue, Charles E. ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6790-6791

[9] Copper-Catalyzed Synthesis of Azaspirocyclohexadienones from α-Azido-N-arylamides under an Oxygen Atmosphere [J].

Chiba, Shunsuke ;

Zhang, Line ;

Lee, Jian-Yuan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (21) :7266-+

[10] Oxidative amidation of phenols through the use of hypervalent iodine reagents: Development and applications [J].

Ciufolini, Marco A. ;

Braun, Norbert A. ;

Canesi, Sylvain ;

Ousmer, Malika ;

Chang, Jonah ;

Chai, David .

SYNTHESIS-STUTTGART, 2007, (24) :3759-3772

← 1 2 3 4 5 →