Chiral discrimination in hydrogen-bonded [7]helicenes

被引:123
作者
Murguly, E [1 ]
McDonald, R [1 ]
Branda, NR [1 ]
机构
[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada
关键词
D O I
10.1021/ol006366y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A series of racemic [7]helicenes have been prepared and characterized both in solution and in the solid state. Despite the helicenes having the ability to self-assemble in a variety of stereochemical and topological relationships, they formed only enantiomerically pure dimers held together by two pairs of cooperative hydrogen bonds. The self-assembly process was enantiospecific in solution and diastereoselective in the crystal.
引用
收藏
页码:3169 / 3172
页数:4
相关论文
共 25 条
[1]  
Cuccia LA, 2000, ANGEW CHEM INT EDIT, V39, P233, DOI 10.1002/(SICI)1521-3773(20000103)39:1<233::AID-ANIE233>3.0.CO
[2]  
2-R
[3]   SYNTHESIS OF THE HELICOPODANDS - NOVEL SHAPES FOR CHIRAL CLEFTS [J].
DESHAYES, K ;
BROENE, RD ;
CHAO, I ;
KNOBLER, CB ;
DIEDERICH, F .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (24) :6787-6795
[4]   Application of the Russig-Laatsch reaction to synthesize a bis[5]helicene chiral pocket for asymmetric catalysis [J].
Dreher, SD ;
Katz, TJ ;
Lam, KC ;
Rheingold, AL .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (03) :815-822
[5]  
Eliel E. L., 1994, STEREOCHEMISTRY ORGA, P1121
[6]   Helical twist sense bias in oligo(phenylene ethynylene)s induced by an optically active flexible tether [J].
Gin, MS ;
Moore, JS .
ORGANIC LETTERS, 2000, 2 (02) :135-138
[7]   SOLID-STATE COLUMNS MADE FROM TWISTED, SELF-COMPLEMENTARY TERPYRIDINE UNITS [J].
HUANG, CY ;
LYNCH, V ;
ANSLYN, EV .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1992, 31 (09) :1244-1246
[8]   Racemization barriers of helicenes: A computational study [J].
Janke, RH ;
Haufe, G ;
Wurthwein, EU ;
Borkent, JH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (25) :6031-6035
[9]   SYNTHESIS AND PROPERTIES OF OPTICALLY-ACTIVE HELICAL METALLOCENE OLIGOMERS [J].
KATZ, TJ ;
SUDHAKAR, A ;
TEASLEY, MF ;
GILBERT, AM ;
GEIGER, WE ;
ROBBEN, MP ;
WUENSCH, M ;
WARD, MD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (08) :3182-3198
[10]  
Katz TJ, 2000, ANGEW CHEM INT EDIT, V39, P1921, DOI 10.1002/1521-3773(20000602)39:11<1921::AID-ANIE1921>3.0.CO