Cyclodextrin molecular reactors

被引:48
作者
Barr, L
Dumanski, PG
Easton, CJ [1 ]
Harper, JB
Lee, K
Lincoln, SF
Meyer, AG
Simpson, JS
机构
[1] Australian Natl Univ, Res Sch Chem, Canberra, ACT 0200, Australia
[2] Univ Adelaide, Dept Chem, Adelaide, SA 5005, Australia
关键词
catalysts; controlled assembly; cyclodextrins; molecular reactors; regioselectivity; self-assembly; templates;
D O I
10.1007/s10847-003-8833-9
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The ability of cyclodextrins to form inclusion complexes with hydrophobic species in aqueous solution makes them well-suited to the development of molecular reactors, to be used as miniature reaction vessels in order to control the outcomes of chemical transformations at the molecular level. In this manner, reaction rates can be increased and products may be obtained that are different to those normally accessible from reactions in free solution. Examples used to illustrate these effects include: the application of cyclodextrins to control the regioselectivity of bromination of aromatic substrates with pyridinium dichlorobromate; the use of a metallocyclodextrin to increase the rate of hydrolysis of a phosphate triester by almost five orders of magnitude; the development of modified cyclodextrins to increase the rates and reverse the regioselectivity of nitrile oxide cycloadditions; and the use of a cyclodextrin dimer to change the ratio of formation of indigoid dyes by a factor of more than 3500.
引用
收藏
页码:19 / 24
页数:6
相关论文
共 34 条
[1]  
[Anonymous], 1971, BIOORG CHEM, DOI [10.1016/0045-2068(71)90012-5, DOI 10.1016/0045-2068(71)90012-5]
[2]  
[Anonymous], 1984, J INCLUSION PHENOM M, DOI DOI 10.1007/BF00662250
[3]   Metallocyclodextrin catalysts for hydrolysis of phosphate triesters [J].
Barr, L ;
Easton, CJ ;
Lee, K ;
Lincoln, SF ;
Simpson, JS .
TETRAHEDRON LETTERS, 2002, 43 (43) :7797-7800
[4]   SELECTIVE AROMATIC SUBSTITUTION WITHIN A CYCLODEXTRIN MIXED COMPLEX [J].
BRESLOW, R ;
CAMPBELL, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (11) :3085-&
[5]  
BRESLOW R, 1976, TETRAHEDRON LETT, P1645
[6]   Biomimetic reactions catalyzed by cyclodextrins and their derivatives [J].
Breslow, R ;
Dong, SD .
CHEMICAL REVIEWS, 1998, 98 (05) :1997-2011
[7]   CHLORINATION OF ACETANILIDE AND BENZANILIDE IN THE PRESENCE OF CYCLODEXTRINES AND AMYLOSE [J].
CHENEVERT, R ;
AMPLEMAN, G .
CANADIAN JOURNAL OF CHEMISTRY, 1987, 65 (02) :307-310
[8]   Effect of cyclodextrins on electrophilic aromatic bromination in aqueous solution [J].
Dumanski, PG ;
Easton, CJ ;
Lincoln, SF ;
Simpson, JS .
AUSTRALIAN JOURNAL OF CHEMISTRY, 2003, 56 (11) :1107-1111
[9]  
Easton C. J., 1999, MODIFIED CYCLODEXTRI
[10]   N,N′-bis(6A-deoxy-β-cyclodextrin-6A-yl)urea as a molecular template in the formation of indigoid dyes [J].
Easton, CJ ;
Harper, JB ;
Lincoln, SF .
NEW JOURNAL OF CHEMISTRY, 1998, 22 (11) :1163-1165