Synthesis and Application of β-Substituted Pauson-Khand Adducts: Trifluoromethyl as a Removable Steering Group

被引:25
作者
Aiguabella, Nuria [1 ]
del Pozo, Carlos [3 ,4 ]
Verdaguer, Xavier [1 ,2 ]
Fustero, Santos [3 ,4 ]
Riera, Antoni [1 ,2 ]
机构
[1] Inst Res Biomed IRB Barcelona, Barcelona 08028, Spain
[2] Univ Barcelona, Dept Quim Organ, E-08028 Barcelona, Spain
[3] Univ Valencia, Dept Quim Organ, E-46100 Burjassot, Spain
[4] Ctr Invest Principe Felipe, Lab Mol Organ, Valencia 46012, Spain
关键词
directing group; PausonKhand reaction; regioselectivity; synthetic methods; trifluoromethyl alkynes; ENANTIOSELECTIVE RING CONSTRUCTION; CONJUGATE ADDITION; EFFICIENT; (-)-ALPHA-CUPARENONE; REGIOSELECTIVITY; CARBON; REGIOCHEMISTRY; REACTIVITY; COMPLEXES; LIGANDS;
D O I
10.1002/anie.201300907
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Against the rules: The synthesis of the previously unknown β-substituted regioisomers of the intermolecular Pauson-Khand reaction of terminal alkynes is reported. This regiochemistry was achieved by using the trifluoromethyl group as a removable directing group on the alkyne. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:5355 / 5359
页数:5
相关论文
共 47 条
[1]   Low-energy pathway for Pauson-Khand reactions:: Synthesis and reactivity of dicobalt hexacarbonyl complexes of chiral ynamines [J].
Balsells, J ;
Vázquez, J ;
Moyano, A ;
Pericàs, MA ;
Riera, A .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (22) :7291-7302
[2]   The Pauson-Khand reaction, a powerful synthetic tool for the synthesis of complex molecules [J].
Blanco-Urgoiti, J ;
Añorbe, L ;
Pérez-Serrano, L ;
Domínguez, G ;
Pérez-Castells, J .
CHEMICAL SOCIETY REVIEWS, 2004, 33 (01) :32-42
[3]   An efficient and practical total synthesis of (±)-α-cuparenone [J].
Chavan, Subhash P. ;
Dhawane, Abasaheb N. ;
Kalkote, Uttam R. .
SYNTHESIS-STUTTGART, 2007, 24 (24) :3827-3830
[4]  
CHETTY GL, 1964, TETRAHEDRON LETT, P73
[5]   Copper-Mediated Aerobic Oxidative Trifluoromethylation of Terminal Alkynes with Me3SiCF3 [J].
Chu, Lingling ;
Qing, Feng-Ling .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (21) :7262-+
[6]   First C-C bond formation in the Pauson-Khand reaction: Influence of carbon-carbon triple bond polarization on regiochemistry - A density functional theory study [J].
de Bruin, Theodorus J. M. ;
Michel, Carine ;
Vekey, Karoly ;
Greene, Andrew E. ;
Gimbert, Yves ;
Milet, Anne .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (20) :4281-4288
[7]   Insight into the reactivity of olefins in the Pauson-Khand reaction [J].
de Bruin, TJM ;
Milet, A ;
Greene, AE ;
Gimbert, Y .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (04) :1075-1080
[8]   Theoretical study of the regiochemistry-determining step of the Pauson-Khand reaction [J].
de Bruin, TJM ;
Milet, A ;
Robert, F ;
Gimbert, Y ;
Greene, AE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (29) :7184-7185
[9]   Electronic Regioselectivity of Diarylalkynes in Cobalt-Mediated Pauson-Khand Reaction: An Experimental and Computational Study with Para- and Meta-Substituted Diarylalkynes and Norbornene [J].
Fager-Jokela, Erika ;
Muuronen, Mikko ;
Patzschke, Michael ;
Helaja, Juho .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (20) :9134-9147
[10]  
FLEMMING S, 1995, SYNTHESIS-STUTTGART, P317