Highly facile regioselective ring opening of epoxides to halohydrins in the presence of polyhipes (CTAB) and β-cyclodextrins (TSAX) in water

Current Organic Chemistry

Volumn 15, Issue 15, 2011, Pages 2690-2693

  Zhang, Shengmiao ^a   Chen, Jianding ^a   Perchyonok, V Tamara ^a  

^a VTPChem PTy Ltd   (Australia)

Author keywords

Epoxides; PolyHIPEs; Water; cyclodextrins

Indexed keywords

REGIOSELECTIVITY;

AMMONIUM HALIDES; AQUEOUS MEDIA; EPOXIDE; HALOHYDRINS; POLYHIPE; REGIOSELECTIVE RING OPENING; RING OPENING OF EPOXIDE; Β-CYCLODEXTRIN;

CYCLODEXTRINS;

EID: 79959951659     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527211796367264     Document Type: Article

References (34)

1. Barlett, P. A. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: Orlando, Fl, 1984; Vol. 3, p 411.
2. Erden, I. Comprehensive Heterocyclic Chemistry, 2nd ed.; Padwa, A. Ed.; Pergamon: Oxford, 1996; Vol. 1A, Chapter
3. Watson, K. G.; Fung, Y. M.; Gredley, M.; Bird, G. J.; Jackson, W.R.; Gountzos, H.; Matthews, B. R. Asymmetric syntheses of (+)-diltiazem hydrochloride. Chem. Commun., 1990, 1018;
4. Kolb, H. C.; Sharpless, K. B. A simplified procedure for the stereospecific transformation of 1,2-diols into epoxides, Tetrahedron, 1992, 48, 10515;
5. Know, D. W.; Cho, M. S.; Kim, Y. H. Samarium(III) Iodide Complex Catalyzed Regioselective Cleavage of Epoxides to Iodohydrins: Tandem Epoxide Opening-Iodocyclization. Synlett, 2003, 959;
6. 2- Type Ring-Opening of Epoxides with TBABF-KHF2, Synlett, 2003, 1530.
7. Moore, R. E., Marine Natural Products; Scheuer, P. J., Ed.; Academic: New York, 1978; Vol. 1, Chapter 2.
8. Fenical, W. Marine Natural Products; Scheuer, P. J., Ed.; Academic: New York, 1980; Vol. 2, p.174.
9. Stewart, C.A.; Vanderwerf, C.A. Reaction of propylene oxide with hydrogen halides. J. Am. Chem. Soc., 1954, 76, 1259;
10. Smith, J. G.; Fieser, M. Fieser and Fieser's Reagent for Organic Synthess; John Wiely and Sons: New York, 1990; Vol. 1-12.
11. Kotsuki, H.; Shimanouchi, T.; Ohshima, R.; Fujivara, S. Solvent-free organic reactions on silica gel supports. Facile transformation of epoxides to β-halohydrins with lithium halides. Tetrahedron, 1998, 54, 2709;
12. Kotsuki, H.; Shimanouchi, T. A facile conversion of epoxides to β-halohydrins with silica gel-supported lithium halides. Tetrahedron Lett., 1996, 37, 1845;
13. Shimizu, M.; Yoshida, A.; Fujisawa, T. Regioselective conversion of epoxides to halohydrins by titanium(iv) halide-lithium halide complex. Synlett., 1992, 204.
14. Sabitha, B.; Sateesh, R.; Rajkumar, M.; Reddy, Ch S.; Yadav, J. S. Highly regioselective ring opening of epoxides and aziridines using cerium(iii) chloride. Tetrahedron Lett., 2001, 42, 3955.
15. Andrews, G. C.; Grawford, T. C.; Contilio Jr, L. G. Nucleophilic catalysis in the insertion of silicon halides into oxiranes: A synthesis of o-protected vicinal halohydrins. Tetrahedron Lett., 1981, 22, 3803.
16. Coxon, J. N.; Harthson, M.P.; Rae, W.J. Reactions of epoxides-XXVI: The BF3-catalysed rearrangement of 5,6 α-epoxy-6 α -phenyl-5 β-cholestane and a novel ketone rearrangement. Tetrahedron, 1970, 26, 1091.
17. Suh, Y-G.; Koo, B-A.; Ko, J-A.; Cho, Y-S. A Facile and Highly Regioselective Conversion of Epoxides to Bromohydrins Using Tetrabutylammonium Bromide and Magnesium Nitrate. Chem. Lett., 1993, 1907.
18. Iranpoor, N.; Firouzabadi, H.; Aghapour, G.; Nahid, A. Unsymmetrical dihalides by triphenylphosphene/2,3-dichloro-5,6-dicyano1,4-benzoqunone (ddq) in the presence of quaternary ammonium halides. Bull. Chem. Soc. Jpn., 2004, 77, 1885.
19. Breslow, R.; Dong, S. D. Biomimetic reactions catalyzed by. Cyclodextrins and their derivatives. Chem. Rev., 1998, 98, 1997.
20. Easton, C. J.; Lincoln, S.F. Modified cyclodextrins: scaffolds and templates for supramolecular chemistry, imperial college press: London, 1999.
21. Barr, L.; Dumanski, P.G.; Easton, C. J.; Harper, J. B.; Lee, K.; Lincoln, S. F.; Meyer, A. G; Simpson, J. S. Cyclodextrins complexation of the stilbene 4-(2-(4-tertbutylphenyl) ethen-1-yl)- benzoate and the self-assembly of molecular devices. J. Inclusion Phenom. Macrocyc. Chem., 2004, 50, 19.
22. Easton, C.J.; Lincoln, S. F.; Barr, L.; Onagi, H. Molecular reactors and machines: applications, potential, and limitations. Chem. Eur. J., 2004, 10, 3120.
23. Perchyonok, V. T. Radical reactions in aqueous media, RSC. Clark J.; Kraus G., 2010, http://www.rsc.org/Shop/books/2009/9781849730006.asp
24. Cameron N. R. High internal phase emulsion templating as a route to welldefined porous polymers. Polymer, 2005, 46, 1439-1449.
25. Zhang H.; Cooper A. I. Synthesis and applications of emulsion-templated porous materials. Soft Matter, 2005, 1, 107-113.
26. Zhang S.; Chen J. Synthesis of open porous emulsion-templated monoliths using cetyltrimethylammonium bromide. Polymer, 2007, 48, 3021-3025.
27. Zhang S.; Chen J.; Perchyonok V.T. Stability of high internal phase emulsions with sole cationic surfactant and its tailoring morphology of porous polymers based on the emulsions. Polymer, 2009, 50, 1723-1731.
28. Zhang, S.; Chen, J.; Perchyonok, V.T. PolyHIPEs as novel media for conventional free radical chemistry. Lett. Org. Chem., 2008, 5(4), 304-307.
29. Deleuze, H.; Mailard, B.; Mondain-Monval, O. Development of a new ultraporous polymer as support in organic synthesis. Bioorg. Med. Chem. Lett. 2002, 12(14), 1877-1880.
30. Surendra K., Srilakshmi Krishnaveni. N., Pavan Kumar, V., Nageswar, Y. V. D., Rama Rao, K. Regioselective ring opening of oxiranes to halohydrins with tetrabutylammonium halide in water in the presence of β-cyclodextrins. Lett. Org. Chem., 2005, 2, 652-658.
31. Reddy, M. A.; Bhanumathi, N.; Rao, K. R. Asymmetric synthesis of 2-azido-1-arylethanols from aryl azido ketone-cyclodextrin complexes and sodium borohydride in water. Chem. Commun., 2001, 1974.
32. Reddy, L. R., Bhanumathi, N.; Rao, K. R. Dynamic kinetic asymmetric synthesis of aminoalcohols from racemic epoxides in cyclodextrin complexes under solid state conditions. Chem. Commun., 2000, 2321,
33. Reddy, L. R.; Reddy, M. A. Bhanumathi, N.; Rao, K. R. Regioselective ring-opening of aziridines with thiophenol in the presence of β-cyclodextrin in water. Synlett, 2000, 339.
34. E. D. Reddy L.R.; Bhanumathi, N.; Rao K. R. Highly regioselective ring opening of oxiranes with phenoxides in the presence of β-cyclodextrin in water. New J. Chem., 2001, 25, 359.