Visible light induced intermolecular [2+2]-cycloaddition reactions of 3-ylideneoxindoles through energy transfer pathway

被引：141
作者：
Zou, You-Quan [1 ]
Duan, Shu-Wen [1 ]
Meng, Xiang-Gao [1 ]
Hu, Xiao-Qiang [1 ]
Gao, Shuang [1 ]
Chen, Jia-Rong [1 ]
Xiao, Wen-Jing [1 ,2 ]
机构：
[1] Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Hubei, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
来源：
TETRAHEDRON | 2012年 / 68卷 / 34期
基金：
美国国家科学基金会;
关键词：
Visible light; Cycloaddition; Photocatalysis; Energy transfer; Spirocyclic oxindole; C-H FUNCTIONALIZATION; PHOTOREDOX CATALYSIS; COORDINATION-COMPOUNDS; 2+2 CYCLOADDITIONS; DIELS-ALDER; ELECTRON; STATE; PHOTOCHEMISTRY; PHOTOCATALYSIS; LUMINESCENCE;
D O I：
10.1016/j.tet.2012.06.011
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly diastereoselective and regioselective [2+2]-cycloaddition reaction of 3-ylideneoxindoles has been accomplished using visible light photocatalysis. This visible light photocatalytic protocol allows an expedient access to diversely functionalized and structurally constrained oxindole derivatives containing two spirocycles and four stereogenic centers, including two all-carbon quaternary centers. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6914 / 6919
页数：6
相关论文
共 105 条
[1]  
Alper PB, 1999, ANGEW CHEM INT EDIT, V38, P3186, DOI 10.1002/(SICI)1521-3773(19991102)38:21<3186::AID-ANIE3186>3.0.CO
[2]  
2-E
[3]   Investigating the Rate of Photoreductive Glucosyl Radical Generation [J].
Andrews, R. Stephen ;
Becker, Jennifer J. ;
Gagne, Michel R. .
ORGANIC LETTERS, 2011, 13 (09) :2406-2409
[4]   Intermolecular Addition of Glycosyl Halides to Alkenes Mediated by Visible Light [J].
Andrews, R. Stephen ;
Becker, Jennifer J. ;
Gagne, Michel R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (40) :7274-7276
[5]   Intramolecular [2+2] Photocycloaddition of Substituted Isoquinolones: Enantioselectivity and Kinetic Resolution Induced by a Chiral Template [J].
Austin, Kerrie A. B. ;
Herdtweck, Eberhardt ;
Bach, Thorsten .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (36) :8416-8419
[6]   Enantioselective intermolecular [2+2]-photocycloaddition reactions of alkenes and a 2-quinolone in solution [J].
Bach, T ;
Bergmann, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (46) :11525-11526
[7]  
Bach T, 2000, ANGEW CHEM INT EDIT, V39, P2302, DOI 10.1002/1521-3773(20000703)39:13<2302::AID-ANIE2302>3.3.CO
[8]  
2-Y
[9]  
Bach T, 1998, SYNTHESIS-STUTTGART, P683
[10]   BIMOLECULAR ELECTRON-TRANSFER PROCESSES OF ELECTRONICALLY EXCITED TRIS(2,2'-BIPYRIDINE)CHROMIUM(III) [J].
BALLARDINI, R ;
VARANI, G ;
SCANDOLA, F ;
BALZANI, V .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (23) :7432-7433
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