Stereospecific Palladium-Catalyzed Decarboxylative C(sp3)-C(sp2) Coupling of 2,5-Cyclohexadiene-1-carboxylic Acid Derivatives with Aryl Iodides

被引:27
作者
Chou, Chih-Ming [1 ]
Chatterjee, Indranil [1 ]
Studer, Armido [1 ]
机构
[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany
关键词
asymmetric synthesis; Birch reduction; C-C bond formation; homogeneous catalysis; palladium; KOCH-HAAF CARBOXYLATIONS; METALATED CYCLOHEXADIENES; REDUCTION-ALKYLATION; ALLYLIC ALKYLATION; BIRCH REDUCTION; DESYMMETRIZATION; ALLYLATION; OLEFINATION; HALIDES;
D O I
10.1002/anie.201103450
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Walk on the same side! The title reaction occurs by means of highly stereospecific 1,3-metal migration. The starting carboxylic acids are readily prepared by Birch reduction, and the developed protocol provides an efficient route to enantiomerically pure 5-arylated-1,3-cyclohexadiene derivatives (see scheme). Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:8614 / 8617
页数:4
相关论文
共 58 条
[1]  
[Anonymous], 2009, ANGEW CHEM
[2]  
[Anonymous], 2011, ANGEW CHEM
[3]  
[Anonymous], 2011, ANGEW CHEM INT EDIT
[4]   A Novel Iron-Catalyzed Decarboxylative Csp3-Csp2 Coupling of Proline Derivatives and Naphthol [J].
Bi, Hai-Peng ;
Chen, Wen-Wen ;
Liang, Yong-Min ;
Li, Chao-Jun .
ORGANIC LETTERS, 2009, 11 (15) :3246-3249
[5]   The Copper-Catalyzed Decarboxylative Coupling of the sp3-Hybridized Carbon Atoms of α-Amino Acids [J].
Bi, Hai-Peng ;
Zhao, Liang ;
Liang, Yong-Min ;
Li, Chao-Jun .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (04) :792-795
[6]   Synthesis of homoallylic amines via the palladium-catalyzed decarboxylative coupling of amino acid derivatives [J].
Burger, Erin C. ;
Tunge, Jon A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (31) :10002-10003
[7]   Copper-Catalyzed Enantioselective [2+2] Cycloadditions of 2-Nitrosopyridine with Ketenes [J].
Chatterjee, Indranil ;
Jana, Chandan Kumar ;
Steinmetz, Marc ;
Grimme, Stefan ;
Studer, Armido .
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (06) :945-948
[8]   Palladium-Catalyzed Decarboxylative Benzylation of Diphenylglycinate Imines [J].
Fields, Wendy H. ;
Chruma, Jason J. .
ORGANIC LETTERS, 2010, 12 (02) :316-319
[9]   Unexpected intermolecular Pd-catalyzed cross-coupling reaction employing heteroaromatic carboxylic acids as coupling partners [J].
Forgione, Pat ;
Brochu, Marie-Christine ;
St-Onge, Miguel ;
Thesen, Kris H. ;
Bailey, Murray D. ;
Bilodeau, Francois .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (35) :11350-11351
[10]  
Gooβen, 2008, ANGEW CHEM, V120, P3144, DOI DOI 10.1002/ANGE.200704782