Synthesis, Chiral Separation, and Absolute Configuration of Bis-(N-aryl) Atropisomeric Triads: 1,2-Bis-[4-methyl-2-(thi)oxo-2,3-dihydrothiazol-3-yl]-benzene

被引：6
作者：
Roussel, Christian [1 ]
Kaid-Slimane, Radia [1 ]
Andreoli, Federico [1 ]
Renaudin, Mailis [1 ]
Vanthuyne, Nicolas [1 ]
机构：
[1] Univ Paul Cezanne, UMR Chirosci 6263, Lab Stereochim Dynam & Chiralite, F-13397 Marseille 20, France
来源：
CHIRALITY | 2009年 / 21卷 / 01期
关键词：
atropisomer; molecular triads; absolute configuration; chiral HPLC; barrier to rotation; heterocycles; TRANS ROTATIONAL ISOMERS; COFACIAL AROMATIC RINGS; STABILIZING INTERACTIONS; DYNAMIC NMR; C-N; BARRIERS; PI; STEREODYNAMICS; DERIVATIVES; SALTS;
D O I：
10.1002/chir.20599
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
In this work, a series of 1,2-bis-[4-methyl-2-(thi)oxo-2,3-dihydrothiazol-3-yl]-benzene has been prepared. These atropisomeric molecular triads were exclusively found to exist in the anti-form. They were separated into enantiomers by liquid chromatography on a chiral support. The absolute configurations of the enantiomers were determined using a chemical correlation method together with chiral chromatography. The barriers to interconversion of the enantiomers were determined. Chirality 21:160166,2009. (C) 2008 Wiley-Liss, Inc.
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收藏
页码：160 / 166
页数：7
相关论文
共 60 条
[1]   Cathodic synthesis of powerful electron π-donors including dithiadiazafulvalenes [J].
Bellec, N ;
Lorcy, D ;
Robert, A ;
Carlier, R ;
Tallec, A .
JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1999, 462 (02) :137-142
[2]   Chemical and electrochemical investigations on thiazolium salts:: a route to powerful donors in the dithiadiazafulvalene series [J].
Bellec, N ;
Guérin, D ;
Lorcy, D ;
Robert, A ;
Carlier, R ;
Tallec, A .
ACTA CHEMICA SCANDINAVICA, 1999, 53 (10) :861-866
[3]  
BELLEC N, 1998, SYNTHESIS-STUTTGART, V10, P1142
[4]   Ab initio study of atropisomers of some derivatives of 1,8-disubstituted biphenylenes and naphthalenes [J].
Bigdeli, Mohammad A. ;
Moradi, Shahram ;
Nemati, Firouzeh .
JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2007, 807 (1-3) :125-135
[5]   Synthesis of 4,5-diarylquinazolines:: a system with cofacial aromatic rings.: Diazines.: Part 39 [J].
Busch, A ;
Chapoulaud, VG ;
Audoux, J ;
Plé, N ;
Turck, A .
TETRAHEDRON, 2004, 60 (25) :5373-5382
[6]   Synthesis, chiral HPLC resolution and configuration assignment of 1-phenylglyceryl trinitrate stereomers [J].
Chegaev, Konstantin ;
Lazzarato, Loretta ;
Tron, Gian Cesare ;
Marabello, Domenica ;
Di Stilo, Antonella ;
Cena, Clra ;
Fruttero, Roberta ;
Gasco, Alberto ;
Vanthuyne, Nicolas ;
Roussel, Christian .
CHIRALITY, 2006, 18 (06) :430-436
[7]   STABLE CIS AND TRANS ROTATIONAL ISOMERS OF 1,8-DI-ORTHO-TOLYLNAPHTHALENE [J].
CLOUGH, RL ;
ROBERTS, JD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (04) :1018-1020
[8]   INTERACTION BETWEEN STACKED ARYL GROUPS IN 1,8-DIARYLNAPHTHALENES - DOMINANCE OF POLAR/PI OVER CHARGE-TRANSFER EFFECTS [J].
COZZI, F ;
SIEGEL, JS .
PURE AND APPLIED CHEMISTRY, 1995, 67 (05) :683-689
[9]   Conformational studies by dynamic NMR.: 86.: Structure, stereodynamics, and cryogenic enantioseparation of the stereolabile isomers of o-dinaphthylphenyl derivatives [J].
Dell-Erba, C ;
Gasparrini, F ;
Grilli, S ;
Lunazzi, L ;
Mazzanti, A ;
Novi, M ;
Pierini, M ;
Tavani, C ;
Villani, C .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (05) :1663-1668
[10]  
GALLO R, 1988, ADV HETEROCYCL CHEM, V43, P173
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