Residual Dipolar Couplings as a Powerful Tool for Constitutional Analysis: The Unexpected Formation of Tricyclic Compounds

被引:70
作者
Kummerloewe, Grit [1 ]
Crone, Benedikt [1 ]
Kretschmer, Manuel [1 ]
Kirsch, Stefan F. [1 ]
Luy, Burkhard [1 ]
机构
[1] Tech Univ Munich, Dept Chem, D-85747 Garching, Germany
关键词
electrophiles; enynes; NMR spectroscopy; residual dipolar couplings; structure elucidation; INTRAMOLECULAR SCHMIDT REACTIONS; RELATIVE CONFIGURATION; ORGANIC-MOLECULES; NMR; ASSIGNMENT; ALIGNMENT; AZIDES; RDCS; CONFORMATION; CYCLIZATION;
D O I
10.1002/anie.201007305
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Analyze this! Residual dipolar couplings (RDCs) can be used to determine the constitution of a small molecule when traditional methods for structure elucidation fail. In a case study, a highly congested, tricyclic compound resulting from the electrophilic cyclization of an azide-containing 1,5-enyne was investigated. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:2643 / 2645
页数:3
相关论文
共 40 条
[1]   Weakly oriented liquid-crystal NMR solvents as a general tool to determine relative configurations [J].
Aroulanda, C ;
Boucard, V ;
Guibé, F ;
Courtieu, J ;
Merlet, D .
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (18) :4536-4539
[2]   IODINE-INDUCED STEREOSELECTIVE CARBOCYCLIZATIONS - A NEW METHOD FOR THE SYNTHESIS OF CYCLOHEXANE AND CYCLOHEXENE DERIVATIVES [J].
BARLUENGA, J ;
GONZALEZ, JM ;
CAMPOS, PJ ;
ASENSIO, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (11) :1546-1547
[3]  
Barluenga J., 1988, ANGEW CHEM, V100, P1604
[4]   ASSIGNMENT OF C-13 NMR-SPECTRA VIA DOUBLE-QUANTUM COHERENCE [J].
BAX, A ;
FREEMAN, R ;
FRENKIEL, TA ;
LEVITT, MH .
JOURNAL OF MAGNETIC RESONANCE, 1981, 43 (03) :478-483
[5]  
Crone B., 2010, ANGEW CHEM, V122, P4765
[6]   Electrophilic Cyclization of 1,5-Enynes [J].
Crone, Benedikt ;
Kirsch, Stefan F. ;
Umland, Klaus-Daniel .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (27) :4661-4664
[7]   The CLIP/CLAP-HSQC: Pure absorptive spectra for the measurement of one-bond couplings [J].
Enthart, Andreas ;
Freudenberger, J. Christoph ;
Furrer, Julien ;
Kessler, Horst ;
Luy, Burkhard .
JOURNAL OF MAGNETIC RESONANCE, 2008, 192 (02) :314-322
[8]  
Fares C., 2008, ANGEW CHEM-GER EDIT, V120, P3782
[9]   Simultaneous determination of the conformation and relative configuration of archazolide A by using nuclear Overhauser effects, J couplings, and residual dipolar couplings [J].
Fares, Christophe ;
Hassfeld, Jorma ;
Menche, Dirk ;
Carlomagno, Teresa .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (20) :3722-3726
[10]   Stretched poly(methyl methacrylate) gel aligns small organic molecules in chloroform.: Stereochemical analysis and diastereotopic proton NMR assignment in ludartin using residual dipolar couplings and 3J coupling constant analysis [J].
Gil, Roberto R. ;
Gayathri, Chakicherla ;
Tsarevsky, Nicolay V. ;
Matyjaszewski, Krzysztof .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (03) :840-848