Recent advance of cyclodextrins as nanoreactors in various organic reactions: A brief overview

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 72, Issue 1-2, 2012, Pages 1-14

  Zhao, Wei ^a   Zhong, Qin ^a  

^a NANJING UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Catalyst; Cyclodextrins; Environmental friendly; Nanoreactor; Organic reaction; Selective catalysis

Indexed keywords

EID: 84862118266     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-011-9983-9     Document Type: Review

References (66)

1. II complexes of catechol-appended b-cyclodextrin derivatives in water. J. Incl. Phenom. Macrocycl. Chem. 54, 41-45 (2006) (Pubitemid 41795816)
2. Tang, W., Tang, J., Choon Ng, S., Chan, H.S.O.: Asymmetric reduction of acetophenones with NaBH4 in the presence of mono-6-(1-methyl-3-imidazolium)-6- deoxy-b-cyclodextrin tos-ylate. J. Incl. Phenom. Macrocycl. Chem. 56, 287-290 (2006)
3. Gould, S., Scott, R.C.: 2-Hydroxypropyl-b-cyclodextrin (HP-b-CD): a toxicology review. Food Chem. Toxicol. 43, 1451-1459 (2005)
4. Takahashi, K.: Organic reactions mediated by cyclodextrins. Chem. Rev. 98, 2013-2033 (1998) (Pubitemid 128633445)
5. Divakar, S., Maheswaran, M.: Applications of cyclodextrins in organic synthesis. J. Sci. Ind. Res. 53, 924-932 (1994)
6. Kano, K.: Selectivities in cyclodextrins chemistry. Bioorg. Chem. Front. 3, 1-23 (1993)
7. Szejtli, J.: Introduction and general overview of cyclodextrins chemistry. Chem. Rev. 98, 1743-1754 (1998)
8. Szejtli, J.: The properties and potential uses of cyclodextrin derivatives. J. Incl. Phenom. Macrocycl. Chem. 14, 25-36 (1992)
9. Hapiot, F., Ponchel, A., Tilloy, S., Monflier, E.: Cyclodextrins and their applications in aqueous-phase metal-catalyzed reactions. C. R. Chim. (2010). doi:10.1016/j.crci.2010.04.003
10. Cacciapaglia, R., Stefano, S.D., Mandolini, L.: Effective molar-ities in supramolecular catalysis of two-substrate reactions. Acc. Chem. Res. 37, 113-122 (2004)
11. Barr, L., Dumanski, P.G., Easton, C.J., Harper, J.B., Lee, K., Lincoln, S.F., Meyer, A.G., Simpson, J.S.: Cyclodextrin molecular reactors. J. Incl. Phenom. Macrocycl. Chem. 50, 19-24 (2004) (Pubitemid 40137312)
12. Surendra, K., Krishnaveni, N.S., Reddy, M.A., Nageswar, Y.V.D., Rao, K.R.: Mild oxidation of alcohols with o-iodoxy-benzoic acid (IBX) in water/acetone mixture in the presence of b-cyclodextrin. J. Org. Chem. 68, 2058-2059 (2003) (Pubitemid 36504876)
13. Surendra, K., Krishnaveni, N.S., Reddy, M.A., Nageswar, Y.V.D., Rao, K.R.: Highly selective oxidation cleavage of b-cyclodextrin-epoxide/aziridine complexes with IBX in water. J. Org. Chem. 68, 9119-9121 (2003) (Pubitemid 37409568)
14. Reddy, M.S., Narender, M., Rao, K.R.: A mild and efficient synthesis of a-tosylamino ketones from aryl aziridines in the presence of b-cyclodextrin and NBS in water. Tetrahedron Lett. 46, 1299-1301 (2005) (Pubitemid 40186745)
15. Ji, H.-B., Shi, D.-P., Shao, M., Li, Z., Wang, L.-F.: Transition metal-free and substrate-selective oxidation of alcohols using water as an only solvent in the presence of b-cyclodextrin. Tetrahedron Lett. 46, 2517-2520 (2005) (Pubitemid 40576214)
16. Surendra, K., Krishnaveni, N.S., Kumar, V.P., Sridhar, R., Rao, K.R.: Selective and efficient oxidation of sulfides to sulfoxides with N-bromosuccinimide in the presence of b-cyclodextrin in water. Tetrahedron Lett. 46, 4581-4583 (2005) (Pubitemid 40779725)
17. Narender, M., Reddy, M.S., Kumar, V.P., Nageswar, Y.V.D., Rao, L.R.: Direct synthesis of carbonyl compounds from THP ethers with IBX in the presence of b-cyclodextrin in water. Tetrahedron Lett. 46, 1971-1973 (2005) (Pubitemid 40311208)
18. Reddy, M.A., Bhanumathi, N., Rao, K.R.: A mild and efficient biomimetic synthesis of a-hydroxymethylarylketones from oxir-anes in the presence of b-cyclodextrin and NBS in water. Tetrahedron Lett. 43, 3237-3238 (2002) (Pubitemid 34310416)
19. Chan, W.-K., Yu, W.-Y., Che, C.-M., Wong, M.-K.: A cyclo-dextrin-modified ketoester for stereoselective epoxidation of alkenes. J. Org. Chem. 68, 6576-6582 (2003) (Pubitemid 37010960)
20. Rousseau, C., Christensen, B., Bols, M: Artificial epoxidase II. Synthesis of cyclodextrin ketoesters and epoxidation of alkenes. Eur. J. Org. Chem. 2734-2739 (2005) (Pubitemid 40976836)
21. Marinescu, L.G., Bols, M.: Very high rate enhancement of benzyl alcohol oxidation by an artificial enzyme. Angew. Chem. Int. Ed. 45, 4590-4593 (2006) (Pubitemid 44106072)
22. 4 in the presence of mono-6-(1-methyl-3- imidazolium)-6-deoxy-b-cyclodextrin tosylate. J. Incl. Phenom. Macrocycl. Chem. 56, 287-290 (2006)
23. Ravichandran, R.: Stereoselective hydrogenation of (2S,5R)-(-)-menthone in the presence of b-cyclodextrin. J. Mol. Catal. A 256, 216-218 (2006) (Pubitemid 44247850)
24. Schlatter, A., Kundu, M.K., Woggon, W.-D.: Enantioselective reduction of aromatic and aliphatic ketones catalyzed by ruthenium complexes attached to b-cyclodextrin. Angew. Chem. Int. Ed. 43, 6731-6734 (2004) (Pubitemid 40019014)
25. Surendra, K., Krishnaveni, N.S., Mahesh, A., Rao, K.R.: Supra-molecular catalysis of Strecker reaction in water under neutral conditions in the presence of b-cyclodextrin. J. Org. Chem. 71, 2532-2534 (2006)
26. Surendra, K., Krishnaveni, N.S., Sridhar, R., Rao, K.R.: Synthesis of b-hydroxysulfides from alkenes under supramolecular catalysis in the presence of b-cyclodextrin in water. J. Org. Chem. 71, 5819-5821 (2006) (Pubitemid 44117041)
27. Surendra, K., Krishnaveni, N.S., Sridhar, R., Rao, K.R.: b-Cyclodextrin promoted aza-Michael addition of amines to conjugated alkenes in water. Tetrahedron Lett. 47, 2125-2127 (2006) (Pubitemid 43287866)
28. Krishnaveni, N.S., Surendra, K., Kumar, V.P., Srinivas, B., Reddy, C.S., Rao, K.R.: b-Cyclodextrin promoted allylation of aldehydes with allyltributyltin under supramolecular catalysis in water. Tetrahedron Lett. 46, 4299-4301 (2005) (Pubitemid 40725409)
29. Pitchumsni, K., Suresh, P.: Per-6-amino-b-cyclodextrin catalyzed asymmetric Michael addition of nitromethane and thiols to chal-cones in water. Tetrahedron Asymmetr. 19, 2037-2044 (2008)
30. Shen, Z., Ma, J., Liu, Y., Jiao, C., Li, M., Zhang, Y.: b-Cyclo-dextrin-immobilized (4S)-phenoxy-(S)-proline as a catalyst for direct asymmetric aldol reactions. Chirality 17, 556-558 (2005) (Pubitemid 41527727)
31. Huang, J., Zhang, X., Armstrong, D.W.: Highly efficient asymmetric direct stoichiometric aldol reactions on/in water. Angew. Chem. Int. Ed. 46, 9073-9077 (2007) (Pubitemid 350232770)
32. Hu, S., Li, J., Xiang, J., Pan, J., Luo, S., Cheng, J.: Asymmetric supramolecular primary amine catalyst in aqueous buffer: connections of selective recognition and asymmetric catalyst. J. Am. Chem. Soc. 132, 7216-7228 (2010)
33. Bricout, H., Caron, L., Bormann, D., Monflier, E.: Substrate-selective catalysis in an aqueous biphasic system with per (2,6-di-O-methyl)-b- cyclodextrin. Catal. Today 66, 355-361 (2001)
34. Binkowski, C., Cabou, J., Bricout, H., Hapiot, F., Monflier, E.: Cleavage of water-insoluble alkylallylcarbonates catalysed by a palladium/TPPTS/ cyclodextrin system: effect of phosphine/cyclodextrin interactions on the reaction rate. J. Mol. Catal. A 215, 23-32 (2004)
35. Leclercq, L., Bricout, H., Tilloy, S., Monflier, E.: Biphasic aqueous organometallic catalysis promoted by cyclodextrin: can surface tension measurements explain the efficiency of chemically modified cyclodextrin. J. Colloid Interf. Sci. 307, 481-487 (2007) (Pubitemid 46175844)
36. Narender, M., Reddy, M.S., Sridhar, R., Nageswar, Y.V.D., Rao, K.R.: Aqueous phase synthesis of thiazoles and aminothiazoles in the presence of b-cyclodextrin. Tetrahedron Lett. 46, 5953-5955 (2005) (Pubitemid 41073450)
37. Murthy, S.N., Madhav, B., Kumar, A.V., Rao, K.R., Nageswar, Y.V.D.: Facile and efficient synthesis of 3,4,5-substituted furan-2(5H)-ones by using b-cyclodextrin as reusable catalyst. Tetrahedron 65, 5251-5256 (2009)
38. Kanagaraj, K., Pitchumani, K.: Solvent-free multicomponent synthesis of pyranopyrazoles: per-6-amino-b-cyclodextrin as a remarkable catalyst and host. Tetrahedron Lett. 51, 3312-3316 (2010)
39. Lopez, O.L., Marinescu, L., Bols, M.: New cup-shaped a-cyclodextrin derivatives and a study of their catalytic properties in oxidation reactions. Tetrahedron 63, 8872-8880 (2007) (Pubitemid 47087863)
40. Kumar, V.P., Reddy, M.S., Narender, M., Surendra, K., Nage-swar, Y.V.D., Rao, K.R.: Aqueous phase mono-protection of amines and amino acid as N-benzyloxycarboxyl derivatives in the presence of b-cyclodextrin. Tetrahedron Lett. 47, 6393-6396 (2006) (Pubitemid 44148721)
41. Suresh, P., Annalakshmi, S., Pitchumani, K.: Regioselective monobromination of substituted phenols in the presence of b-cyclodextrin. Tetrahedron 63, 4959-4967 (2007) (Pubitemid 46669632)
42. Trotta, F., Cravotto, G., Rossignoli, S.: Asymmetric synthesis in the presence of b-cyclodextrin. J. Incl. Phenom. Macrocycl. Chem. 44, 293-296 (2002)
43. Strimbu, L., Liu, J., Kaifer, A.E.: Cyclodextrin-capped palladium nanoparticles as catalysts for the Suzuki reaction. Langmuir 19, 483-485 (2003)
44. Surendra, K., Krishnaveni, N.S., Sridhar, R., Rao, K.R.: Direct Barbier-type allylation of aromatic acetals and dioxolanes in the presence of b-cyclodextrin in water. Tetrahedron Lett. 47, 2133-2136 (2006) (Pubitemid 43287868)
45. Surendra, K., Krishnaveni, N.S., Rao, K.R.: A new and efficient method for the synthesis of thiiranes from oxirane-b-cyclodextrin complexes and thiourea in water. Tetrahedron Lett. 45, 6523-6526 (2004) (Pubitemid 39091081)
46. Narender, M., Surendra, K., Krishnaveni, N.S., Reddy, M.S., Rao, K.R.: A facile regioselective ring opening of aziridines to haloamines using tetrabutylammonium halides in the presence of b-cyclodextrin in water. Tetrahedron Lett. 45, 7995-7997 (2004) (Pubitemid 39303629)
47. Reddy, M.S., Narender, M., Nageswar, Y.V.D., Rao, K.R.: Regioselective ring-opening of aziridines with potassium thio-cyanate in the presence of b-cyclodextrin in water. Tetrahedron Lett. 46, 6437-6439 (2005) (Pubitemid 41175918)
48. Surendra, K., Krishnaveni, N.S., Nageswar, Y.V.D., Rao, K.R.: Highly regioselective ring opening of oxiranes with phenoxides in the presence of b-cyclodextrin in water. J. Org. Chem. 68, 4994-4995 (2003) (Pubitemid 36682739)
49. Sridhar, R., Srinivas, B., Surendra, K., Krishnaveni, N.S., Rao, K.R.: Synthesis of b-hydroxy selenides using benzeneselenol and oxiranes under supramolecular catalysis in the presence of b-cyclodextrin in water. Tetrahedron Lett. 46, 8837-8839 (2005) (Pubitemid 41665912)
50. Reddy, M.S., Srinivas, B., Sridhar, R., Narender, M., Rao, K.R.: Highly regioselective thiolysis of oxiranes under supramolecular involving b-cyclodextrin in water. J. Mol. Catal. A 255, 180-183 (2006) (Pubitemid 44067542)
51. Srinivas, B., Kumar, V.P., Sridhar, R., Surendra, K., Nageswar, Y.V.D., Rao, K.R.: Regioselective nucleophilic opening of epoxides and aziridines under neutral conditions in the presence of b-cyclodextrin in water. J. Mol. Catal. A 261, 1-5 (2007) (Pubitemid 44854627)
52. Ortega-Caballero, F., Rousseau, C., Christensen, B., Petersen, T.E., Bols, M.: Remarkable supramolecular catalysis of glycoside hydrolysis by a cyclodextrin cyanohydrin. J. Am. Chem. Soc. 127, 3238-3239 (2005) (Pubitemid 40365238)
53. Ortega-Caballero, F., Bjerre, J., Laustsen, L.S., Bols, M.: Four orders of magnitude rate increase in artificial enzyme-catalyzed aryl glycoside hydrolysis. J. Org. Chem. 70, 7217-7226 (2005) (Pubitemid 41233258)
54. Bjerre, J., Nielsen, E. H., Bols, M.: Hydrolysis of toxic natural glucosides catalyzed by cyclodextrin dicyanohydrins. Eur. J. Org. Chem. 745-752 (2008)
55. Rousseau, C., Ortega-Caballero, F., Nordstrøm, L.U., Christen-sen, B., Petersen, T.E., Bols, M.: Artificial glycosyl phospho-rylases. Chem. Eur. J. 11, 5094-5101 (2005)
56. Krishnaveni, N.S., Surendra, K., Reddy, M.A., Nageswar, Y.V.D., Rao, K.R.: Highly efficient deprotection of aromatic acetals under neutral conditions using b-cyclodextrin in water. J. Org. Chem. 68, 2018-2019 (2003) (Pubitemid 36504864)
57. Tamaki, T.: Reversible photodimerization of water-soluble anthracenes included in c-cyclodextrin. Chem. Lett. 13, 53-56 (1984)
58. Tamaki, T., Kokubu, T., Ichimura, K.: Regio- and stereoselective photodimerization of anthracenes derivatives included by cyclo-dextrins. Tetrahedron 43, 1485-1494 (1987) (Pubitemid 17063036)
59. Nakamura, A., Inoue, Y.: Supramolecular catalysis of the enan-tiodifferentiating [4?4] photocyclodimerization of 2-anthracene-carboxylate by c-cyclodextrin. J. Am. Chem. Soc. 125, 966-972 (2003) (Pubitemid 36152648)
60. Ikeda, H., Nihei, T., Ueno, A.: Template-assisted stereoselective photocyclodimerization of 2-anthracenecarboxylic acid by bispy-ridinio-appended c-cyclodextrin. J. Org. Chem. 70, 1237-1242 (2005) (Pubitemid 40261360)
61. Nakamura, A., Inoue, Y.: Electrostatic manipulation of enantio-differentiating photocyclodimerization of 2-anthracenecarboxyl-ate within c-cyclodextrin cavity through chemical modification. Inverted product distribution and enhanced enantioselectivity. J. Am. Chem. Soc. 127, 5338-5339 (2005) (Pubitemid 40569843)
62. Ke, C., Yang, C., Mori, T., Wada, T., Liu, Y., Inoue, Y.: Catalytic enantiodifferentiating photocyclodimerization of 2-anthracene-carboxylic acid mediated by non-sensitizing chiral metallosu-pramolecular host. Angew. Chem. Int. Ed. 48, 6675-6677 (2009)
63. Yang, C., Mori, T., Inoue, Y.: Supramolecular enantiodifferenti-ating photocyclodimerization of 2-anthracenecarboxylic mediated by capped c-cyclodextrin: critical control of enantioselectivity by cap rigidity. J. Org. Chem. 73, 5786-5794 (2008)
64. Koodanjeri, S., Pradhan, A.R., Kaanumalle, L.S., Ramamurthy, V.: Cyclodextrin-mediated regioselective photo-Fries reaction of 1-naphthyl phenyl acylates. Tetrahedron 44, 3207-3210 (2003) (Pubitemid 36349604)
65. Galia, A., Navarre, E.C., Scialdone, O., Filardo, G., Monflier, E.: Complexation of phosphine ligands with peracetylated-b-cyclo-dextrin in supercritical carbon dioxide: Effect of temperature and cosolvent on the equilibrium constant. J. Supercrit. Fluids 49, 154-160 (2009)
66. Andreeva, L.V., Maksimov, A.L., Zhuchkova, A.Ya., Predeina, V.V., Filippova, T.Yu., Karakhanov, E.A.: Oxidation of unsatu-rated compounds in ionic liquids with the use of cyclodextrin-containing catalytic system. Pet. Chem. 47, 331-336 (2007) (Pubitemid 47536475)