Non-biaryl atropisomers derived from carbohydrates.: Part 4:: Absolute stereochemistry of carbohydrate-based imidazolidine-2-ones and 2-thiones with axial and central chirality

被引:7
作者
Avalos, M
Babiano, R [1 ]
Cintas, P
Hursthouse, MB
Jiménez, JL
Light, ME
Palaclos, JC
Silvero, G
机构
[1] Univ Extremadura, Dept Quim Organ, E-06071 Badajoz, Spain
[2] Univ Southampton, Dept Chem, Southampton SO17 1BJ, Hants, England
关键词
atropisomerism; carbohydrates; imidazolidines; molecular mechanics; NMR spectroscopy;
D O I
10.1016/j.tet.2005.06.018
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
NMR spectroscopy has proven to be an enabling methodology in elucidating the axial chirality of a series of non-biaryl atropisomers attached to a carbohydrate moiety, based on deshielding effects caused by the aromatic ring. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7945 / 7959
页数:15
相关论文
共 14 条
[1]   Atropisomeric carbohydrate imidazolidines:: a novel class of nonbiaryl atropisomers [J].
Avalos, M ;
Babiano, R ;
Cintas, P ;
Higes, FJ ;
Jiménez, JL ;
Palacios, JC ;
Silvero, G .
TETRAHEDRON-ASYMMETRY, 1999, 10 (21) :4071-4074
[2]   A NOVEL, REGIOSELECTIVE AND HIGHLY STEREOSELECTIVE ANOMERIC DEACETYLATION OF 2-AMINOSUGAR DERIVATIVES [J].
AVALOS, M ;
BABIANO, R ;
CINTAS, P ;
JIMENEZ, JL ;
PALACIOS, JC ;
VALENCIA, C .
TETRAHEDRON LETTERS, 1993, 34 (08) :1359-1362
[3]   Non-biaryl atropisomers derived from carbohydrates.: Part 2.: Atropisomeric behavior of monocyclic and bicyclic imidazolidine-2-ones and 2-thiones [J].
Avalos, M ;
Babiano, R ;
Cintas, P ;
Higes, FJ ;
Jiménez, JL ;
Palacios, JC ;
Silvero, G ;
Valencia, C .
TETRAHEDRON, 1999, 55 (14) :4401-4426
[4]   ON THE MECHANISM OF FORMATION OF GLYCOFURANO[2,1-D]-IMIDAZOLIDIN-2-ONES - REACTION OF 2-AMINO-2-DEOXYHEPTOPYRANOSES WITH ISOCYANATES [J].
AVALOS, M ;
BABIANO, R ;
CINTAS, P ;
JIMENEZ, JL ;
PALACIOS, JC ;
VALENCIA, C .
TETRAHEDRON, 1993, 49 (13) :2676-2690
[5]   CONDENSATION OF 2-AMINO-2-DEOXYSUGARS WITH ISOTHIOCYANATES - SYNTHESIS OF CIS-1,2-FUSED GLYCOPYRANO HETEROCYCLES [J].
AVALOS, M ;
BABIANO, R ;
CINTAS, P ;
JIMENEZ, JL ;
PALACIOS, JC ;
VALENCIA, C .
TETRAHEDRON, 1994, 50 (10) :3273-3296
[6]   THE REACTION OF 2-AMINO-2-DEOXYHEXOPYRANOSES WITH ISOCYANATES, SYNTHESIS OF UREAS AND THEIR TRANSFORMATION INTO HETEROCYCLIC-DERIVATIVES [J].
AVALOS, M ;
BABIANO, R ;
CINTAS, P ;
JIMENEZ, JL ;
PALACIOS, JC ;
VALENCIA, C .
TETRAHEDRON, 1993, 49 (13) :2655-2675
[7]  
AVALOS M, 2005, TETRAHEDRON, V61
[8]   Syntheses with glucosamine. [J].
Bergmann, M ;
Zervas, L .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1931, 64 :975-980
[9]  
Eliel E.L., 1994, STEREOCHEMISTRY ORGA, P1119
[10]  
KALINOWSKI H, 1972, TOP STEREOCHEM, V7, P295