Calix[4]arene-based bis[2]catenanes:: Synthesis and chiral resolution

被引:42
作者
Molokanova, Olena
Bogdan, Anca
Vysotsky, Myroslav O.
Bolte, Michael
Ikai, Tomoyuki
Okamoto, Yoshio
Boehmer, Volker
机构
[1] Univ Mainz, Fachbereich Chem Pharm & Geowissensch, Abt Lehramt Chem, D-55099 Mainz, Germany
[2] Univ Frankfurt, Inst Anorgan Chem, D-60439 Frankfurt, Germany
[3] Nagoya Univ, Inst Sci, Chikusa Ku, Nagoya, Aichi 4648603, Japan
关键词
calixarenes; catenanes; chiral resolution; metathesis; template synthesis;
D O I
10.1002/chem.200601814
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The exclusive formation of hydrogen-bonded dimers between tetraaryl and tetratosylurea calix[4]arenes has been used to prepare a series of ten "bisloop" tetraurea calix[4]arenes 3, in which adjacent phenylurea groups are covalently linked through alpha,omega-dioxyalkane chains. This dimerization with tetratosylurea 2 as template preorganizes the alkenyl residues of tetra(m-alkenyloxyphenyl) ureas 1 and enables their selective connection in high yield (up to 95%) by olefin metathesis followed by hydrogenation. The "bisloop" calixarenes 3 also exclusively form heterodimers with 1. Thus, in a separated metathesis/hydrogenation sequence, a series of 14 cyclic bis[2]catenanes 4, in which two calix[4]arenes are connected through their wide rims by two pairs of interlocked rings (total size 29 to 41 atoms), were prepared in yields of up to 97 %. Optical resolution of these chiral bis[2]catenanes was studied by HPLC on chiral stationary phases. The single-crystal X-ray structure of one example (4(P,10)) confirmed the interlocking rings and revealed that the hydrogen-bonded dimeric capsule of the calix[4]arene can be "completely" opened.
引用
收藏
页码:6157 / 6170
页数:14
相关论文
共 45 条
[1]   OLYMPIADANE [J].
AMABILINO, DB ;
ASHTON, PR ;
REDER, AS ;
SPENCER, N ;
STODDART, JF .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (12) :1286-1290
[2]  
AMABILINO DB, 1994, ANGEW CHEM, V106, P1316
[3]   Templated synthesis of interlocked molecules [J].
Aricó, F ;
Badjic, JD ;
Cantrill, SJ ;
Flood, AH ;
Leung, KCF ;
Liu, Y ;
Stoddart, JF .
TEMPLATES IN CHEMISTRY II, 2005, 249 :203-259
[4]   On the nature of dendrimer cross-linking by ring-closing metathesis [J].
Beil, JB ;
Lemcoff, NG ;
Zimmerman, SC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (42) :13576-13577
[5]   CONFORMATIONAL DYNAMICS OF CALIXARENES - KINETICS OF CONFORMATIONAL INTERCONVERSION IN 5,11,17,23-TETRA-P-TERT-BUTYL-25,26,27,28-TETRAMETHOXYCALIX[4]ARENE UNDER ENTROPIC CONTROL [J].
BLIXT, J ;
DETELLIER, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (26) :11957-11960
[6]   Rational synthesis of multicyclic bis[2]catenanes [J].
Bogdan, A ;
Vysotsky, MO ;
Ikai, T ;
Okamoto, Y ;
Böhmer, V .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (13) :3324-3330
[7]   Topologically novel multiple rotaxanes and catenanes based on tetraurea calix[4]arenes [J].
Bogdan, Anca ;
Rudzevich, Yuliya ;
Vysotsky, Myroslav O. ;
Boehmer, Volker .
CHEMICAL COMMUNICATIONS, 2006, (28) :2941-2952
[8]   Synthesis of huge macrocycles using two calix[4]arenes as templates [J].
Cao, YD ;
Wang, LY ;
Bolte, M ;
Vysotsky, MO ;
Böhmer, V .
CHEMICAL COMMUNICATIONS, 2005, (25) :3132-3134
[9]   A NEW FAMILY OF MOLECULES - METALLO-CATENANES [J].
DIETRICHBUCHECKER, CO ;
SAUVAGE, JP ;
KINTZINGER, JP .
TETRAHEDRON LETTERS, 1983, 24 (46) :5095-5098
[10]   TEMPLATED SYNTHESIS OF INTERLOCKED MACROCYCLIC LIGANDS - THE CATENANDS [J].
DIETRICHBUCHECKER, CO ;
SAUVAGE, JP ;
KERN, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (10) :3043-3045