Helicity inversion in lanthanide(III) complexes with chiral nonaaza macrocyclic ligands

被引:82
作者
Gregolinski, Janusz [1 ]
Lisowski, Jerzy [1 ]
机构
[1] Univ Wroclaw, Dept Chem, PL-50383 Wroclaw, Poland
关键词
chirality; diastereoselectivity; helical structures; lanthanides; macrocyclic ligands;
D O I
10.1002/anie.200602464
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Figure Presented) Giving lanthanides a new twist: The chiral nonaaza macrocycle L wraps tightly around lanthanide(III) ions in a helical fashion (see picture). The all-R enantiomer of the macrocycle, LRRRRRR, forms kinetically controlled complexation products of M helicity (100% de), which undergo inversion to the P diastereomer (90% de). Both products have been isolated in enantiopure form and structurally characterized. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:6122 / 6126
页数:5
相关论文
共 57 条
[1]   Transcription and amplification of molecular chirality to oppositely biased supramolecular π helices [J].
Ajayaghosh, A ;
Varghese, R ;
George, SJ ;
Vijayakumar, C .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (07) :1141-1144
[2]  
Ajayaghosh A., 2006, Angew. Chem, V118, P1159
[3]   Let's twist again - Double-stranded, triple-stranded, and circular helicates [J].
Albrecht, M .
CHEMICAL REVIEWS, 2001, 101 (11) :3457-3497
[4]   Nucleic acid conformation diversity: from structure to function and regulation [J].
Belmont, P ;
Constant, JF ;
Demeunynck, M .
CHEMICAL SOCIETY REVIEWS, 2001, 30 (01) :70-81
[5]   STEREOSELECTIVE SYNTHESIS AND CHARACTERIZATION OF THE OPTICALLY LABILE CHIRAL CR(III) COMPLEX DELTA-(+)589(CR[(-)BDTP]3) [J].
BISCARINI, P ;
KURODA, R .
INORGANICA CHIMICA ACTA, 1988, 154 (02) :209-214
[6]   Dimeric yttrium(III) and neodymium(III) macrocyclic complexes: potential catalysts for hydrolysis of double-stranded DNA [J].
Bligh, SWA ;
Choi, N ;
Evagorou, EG ;
McPartlin, M ;
White, KN .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2001, (21) :3169-3172
[7]   METAL-ION CONTROLLED HELICITY OF AN 18-MEMBERED HEXAAZA TETRAAMINE MACROCYCLE [J].
BLIGH, SWA ;
CHOI, N ;
EVAGOROU, EG ;
LI, WS ;
MCPARTLIN, M .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (20) :2399-2400
[8]   The origin of solvent-controlled supramolecular chirality switching in a Bis(Zinc porphyrin) system [J].
Borovkov, VV ;
Hembury, GA ;
Inoue, Y .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (43) :5310-5314
[9]  
Borovkov VV., 2003, Angew. Chemie, V115, P5468
[10]   Configurationally homogeneous diastereomers of a linear hexa(tertiary phosphine):: Enantioselective self-assembly of a double-stranded parallel helicate of the type (P)-[Cu3(hexaphos)2](PF6)3 [J].
Bowyer, PK ;
Cook, VC ;
Gharib-Naseri, N ;
Gugger, PA ;
Rae, AD ;
Swiegers, GF ;
Willis, AC ;
Zank, J ;
Wild, SB .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2002, 99 (08) :4877-4882