Efficient protocol for stereoselective epoxidation of cinnamic esters using TsNBr2

Synthetic Communications

Volumn 40, Issue 17, 2010, Pages 2647-2652

  Saikia, Indranirekha ^a   Kashyap, Bishwapran ^a   Phukan, Prodeep ^a  

^a GAUHATI UNIVERSITY   (India)

Author keywords

, unsaturated carbonyl compounds; Catalyst free; epoxidation; epoxide; N,N dibromo p toluenesulfonamide (TsNBr2); olefin; styrene

Indexed keywords

BROMINE DERIVATIVE; CINNAMIC ACID; EPOXIDE; N,N DIBROMO 4 TOLUENESULFONAMIDE; STYRENE DERIVATIVE; TOLUENESULFONAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ALKALINITY; ARTICLE; CATALYST; EPOXIDATION; ISOMER; QUANTUM YIELD; REACTION ANALYSIS; REACTION TIME; STEREOCHEMISTRY; SYNTHESIS;

EID: 77955465469     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903318617     Document Type: Article

References (45)

1. Behrens, C. H.; Sharpless, K. B. New transformations of 2,3-epoxy alcohols and related derivatives: Easy routes to homochiral substrates. Aldrichim. Acta 1983, 16, 67-80;
2. Laurt, C; Robert, S. M. Asymmetric epoxidation of a,b-unsaturated ketones catalyzed by poly(amino acids). Aldrichim. Acta 2002, 35, 47-51;
3. Jose, M. C; Molina, M. T.; Shazia, A. Naturally occurring cyclohexane epoxides: Sources, biological activities, and synthesis. Chem. Rev. 2004, 104, 2857-2900;
4. Schwartz, R. E.; Hirsch, C. F.; Sesin, D. F.; Flor, J. E.; Chartrain, M.; Fromtling, R. E.; Harris, G. H.; Salvatore, M. J.; Liesch, J. M.; Yudin, K. Pharmaceuticals from cultured algae. J. Ind. Microbiol. Biotechnol. 1990, 5, 113-123.
5. Sienel, G.; Rieth, R.; Rowbottom, K. T. Ullmann's Encyclopedia of Organic Chemicals; Wiley-VCH: Weinheim, 1999;
6. Lane, B. S.; Burgess, K. Metal-catalyzed epoxidations of alkenes with hydrogen peroxide. Chem. Rev. 2003, 103, 2457-2474.
7. (a) Groves, J. T.; Lee, J.; Marla, S. S. Detection and characterization of an oxomanganese(V) porphyrin complex by rapid-mixing stopped-flow spectrophotometry. J. Am. Chem. Soc. 1997, 119, 6269-6273;
8. Finney, N. S.; Pospisil, P. J.; Chang, S.; Palucki, M.; Konsler, R. G.; Hansen, K. B.; Jacobsen, E. N. On the viability of oxametallacyclic intermediates in the (salen)Mn-catalyzed asymmetric epoxidation. Angew. Chem., Int. Ed. Engl. 1997, 36, 1720-1723;
9. Palucki, M.; Finney, N. S.; Pospisil, P. J.; Gueler, M. L.; Ishida, T.; Jacobsen, E. N. The mechan istic basis for electronic effects on enantioselectivity in the (salen)Mn(III)-catalyzed epox idation reaction. J. Am. Chem. Soc. 1998, 120, 948-954;
10. Lane, B. S.; Burgess, K. A cheap, catalytic, scalable, and environmentally benign method for alkene epoxidations. J. Am. Chem. Soc. 2001, 123, 2933-2934;
11. Lane, B. S.; Vogt, M.; DeRose, V. J.; Burgess, K. Manganese-catalyzed epoxidations of alkenes in bicarbonate solutions. J. Am. Chem. Soc. 2002, 124, 11946-11954;
12. Bosing, M.; Noh, A.; Ina, L.; Krebs, B. Highly efficient catalysts in directed oxygen-transfer processes: Synthesis, structures of novel manganese-containing heteropolyanions and applications in regioselective epoxida tion of dienes with hydrogen peroxide. J. Am. Chem. Soc. 1998,120, 7252-7259;
13. Tong, K.-H.; Wong, K. Y.; Chan, T. H. Manganese/bicarbonate-catalyzed epoxidation of lipo philic alkenes with hydrogen peroxide in ionic liquids. Org. Lett. 2003, 5, 3423-3425;
14. Garcia-Bosch, I.; Company, A.; Fontrodona, X.; Ribas, X.; Costas, M. Efficient and selective peracetic acid epoxidation catalyzed by a robust manganese catalyst. Org. Lett. 2008,10, 2095-2098;
15. 12-, as a remarkably effective catalyst for hydrogen per oxide-mediated oxidations. J. Am. Chem. Soc. 1995, 117, 5066-5074;
16. Kang, B.; Kim, M.; Lee, J.; Do, Y.; Chang, S. Trimanganese complexes bearing bidentate nitrogen ligands as a highly efficient catalyst precursor in the epoxidation of alkenes. J. Org. Chem. 2006, 71, 6721-6727;
17. Nehru, K.; Kim, S. J.; Kim, I. Y.; Seo, M. S.; Kim, Y.; Kim, S.-J.; Kim, J.; Nam, W. A highly efficient non-heme manganese complex in oxygenation reactions. Chem. Commun. 2007, 4623-4625;
18. Tong, K.-H.; Wong, K. Y.; Chan, T. H. Manganese/bicarbonate-catalyzed epoxidation of lipophilic alkenes with hydrogen peroxide in ionic liquids. Org. Lett. 2003, 5, 3423-3425.
19. For copper-catalyzed epoxidaion, see (a) Murahashi, S.; Oda, Y.; Naota, T.; Komiya, N. Aerobic oxidations of alkanes and alkenes in the presence of aldehydes catalysed by copper salts. J. Chem. Soc, Chem. Commun. 1993, 139-140;
20. Minakata, S.; Inaki, K.; Komatsu, M. Aerobic oxidation of olefins to epoxides using a copper(II)-aldehyde system. J. Oleo Sci. 2002, 51, 549-553;
21. (c) Zhu W., Zhang Q., Wang Y. Cu(I)-catalyzed epoxidation of propylene by molecular oxygen. J. Phys. Chem. C, 2008, 112: 7731-7734.
22. For molybdenum-catalyzed epoxidaion, see (a) Ishii, Y.; Yamawaki, K.; Ura, T.; Yamada, H.; Yoshida, T.; Ogawa, M. Hydrogen peroxide oxidation catalyzed by hetero-poly acids combined with cetylpyridinium chloride: Epoxidation of olefins and allylic alcohols, ketonization of alcohols and diols, and oxidative cleavage of 1,2-diols and olefins. J. Org. Chem. 1988, 53, 3581-3593;
23. Chaumette, P.; Mimoun, H.; Saussine, L. Fischer, J.; Mitscheu, A. Peroxo and alkylperoxidic molybdenum(VI) complexes as intermediates in the epoxidation of olefins by alkyl hydroperoxides. J. Organomet. Chem. 1983, 250, 291-310.
24. For tungsten-catalyzed epoxidation, see (a) Sato, K.; Aoki, M.; Ogawa, M.; Hashimoto, T.; Noyori, R. A practical method for epoxidation of terminal olefins with 30% hydrogen peroxide under halide-free conditions.J. Org. Chem. 1996,61, 8310-8311;
25. 3~. J. Am. Chem. Soc. 1995, 117, 681-691;
26. 4- in ionic liquids under microwave irradiation. J. Org. Chem. 2007, 72, 8954-8957.
27. For rhenium-catalyzed epoxidation, see (a) Herrmann, W. A.; Fischer, R. W.; Marz, D. W. Methyltrioxorhenium as catalyst for olefin oxidation. Angew. Chem., Int. Ed. 1991, 30, 1638-1641;
28. Herrmann, W. A.; Fischer, R. W.; Rauch, M. U.; Scherer, W. Multiple bonds between main-group elements and transition metals, 125: Alkylrhenium oxides as homogeneous epoxidation catalysts: Activity, selectivity, stability, deactivation. J. Mol. Catal. 1994, 86, 243-266;
29. 2 and catalytic methyltrioxorhenium/pyridine: Pyridine-mediated ligand acceleration. J. Am. Chem. Soc. 1997, 119, 6189-6190.
30. For vanadium-catalyzed epoxidation, see Zhang, W.; Yamamoto, H. Vanadium-catalyzed asymmetric epoxidation of homoallylic alcohols. J. Am. Chem. Soc. 2007, 129, 286-287.
31. Burke, C. P.; Shu, L.; Shi, Y. An N-aryl-substituted oxazolidinone- containing ketone-catalyzed asymmetric epoxidation with hydrogen peroxide as the primary oxidant. J. Org. Chem. 2007, 72, 6320-6323;
32. Yang, D.; Jiao, G.-S.; Yip, Y.-C; Wong, M.-K. Diastereoselective epoxidation of cyclohexene derivatives by dioxiranes generated in situ: Importance of steric and field effects. J. Org. Chem. 1999, 64, 1635-1639;
33. Hashimoto, N.; Kanda, A. Practical and environmentally friendly epoxidation of olefins using oxone. Org. Process. Res. Dev. 2002, 6, 405-406;
34. Shing, T. K. M.; Leung, G. Y. C; Luk T. Arabinose-derived ketones as catalysts for asymmetric epoxidation of alkenes. J. Org. Chem. 2005, 70, 7279-7289;
35. Imashiro, R.; Seki, M. A catalytic asymmetric synthesis of chiral glycidic acid derivatives through chiral dioxirane-mediated catalytic asymmetric epoxidation of cinnamic acid derivatives. J. Org. Chem. 2004, 69, 4216-4226;
36. Wu, X.-Y.; She, X.; Shi, Y. Highly enantioselective epoxidation of a,P-unsaturated esters by chiral dioxirane. J. Am. Chem. Soc. 2002, 124, 8792-8793.
37. (a) Ho, C.-Y.; Chen, Y.-C; Wong, M.-K.; Yang, D. Fluorinated chiral secondary amines as catalysts for epoxidation of olefins with oxone. J. Org. Chem. 2005, 70, 898-906;
38. Adamo, M. F. A.; Aggarwal, V. K.; Sage, M. A. Epoxidation of alkenes by amine catalyst precursors: Implication of aminium ion and radical cation intermediates. J. Am. Chem. Soc. 2000, 122, 8317-8318;
39. Aggarwal, V. K.; Lopin, C.; Sandrinelli, F. New insights in the mechanism of amine-catalyzed epoxidation: Dual role of protonated ammonium salts as both phase transfer catalysts and activators of oxone. J. Am. Chem. Soc. 2003, 125, 7596-7601.
40. Geng, X.-L.; Wang, Z.; Li, X.-Q.; Zhang, C. A simple method for epoxidation of olefins using sodium chlorite as an oxidant without a catalyst. J. Org. Chem. 2005, 70, 9610-9613.
41. (a) Smith J. G. Synthetically useful reactions of epoxides. Synthesis 1984, 629-656;
42. Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Recent advances in the preparation and synthetic applications of oxiranes. Tetrahedron 1983, 39, 2323-2367.
43. Phukan, P.; Chakraborty, P.; Kataki, D. A simple and efficient method for regioselec-tive and stereoselective synthesis of vicinal bromohydrins and alkoxybromides from olefin. J. Org. Chem. 2006, 71, 7533-7537;
44. 2 without any catalyst. Tetrahedron Lett. 2009, 50, 5083-5087.
45. Nair, C. G. R.; Indrasen, P. New redox titrants in non-aqueous or partially aqueous media\VI: Potentiometric determinations using dibromamine-T and some further applications of dichloramine-T. Talanta 1976, 23, 239-241.