A new catalytic route for the oxidative halogenation of cyclic enol ethers using tungstate exchanged on takovite

Advanced Synthesis and Catalysis

Volumn 347, Issue 1, 2005, Pages 93-104

  Sels, B ^a   Levecque, P ^a   Brosius, R ^a   De Vos, D ^a   Jacobs, P ^a   Gammon, D W ^b   Kinfe, H H ^b  

^a UNIVERSITY OF LEUVEN   (Belgium)

^b UNIVERSITY OF CAPE TOWN   (South Africa)

Author keywords

Cyclic enol ethers; Heterogeneous catalysis; Hydrogen peroxide; Layered double hydroxide; Oxidative halogenation; Tungstate

Indexed keywords

ETHER DERIVATIVE; FURAN DERIVATIVE; HALIDE; HYDROGEN PEROXIDE; MINERAL; PYRAN DERIVATIVE; SUGAR; TAKOVITE; TUNGSTEN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; HALOGENATION; OXIDATION; STEREOCHEMISTRY; SYNTHESIS; TECHNIQUE;

EID: 14644388767     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404138     Document Type: Article

References (62)

1. th edn., Wiley, New York, 2001, p. 1041;
2. b) C. Giardano, G. Castaldi, Org. Chem. 1989, 54, 1470;
3. c) M. F. Ruasse, Acc. Chem. Res. 1990, 23, 87;
4. d) A. Bongini, G. Cainelli, M. Contento, F. Manescalchi, Synthesis 1980, 143;
5. e) M. Smietana, V. Gouverneur, C. Mioskowski, Tetrahedron Lett. 2000, 41, 193;
6. f) A. R. De Corso, B. Panunzi. M. Tingoli, Tetrahedron Lett. 2001, 42, 7245;
7. g) V. A. Mahajan, P. D. Shinde, A. S. Gajare, M. Karthikeyan, R. D. Wakharkar, Green Chem. 2002, 4, 325;
8. h) S. Cerritelli, M. Chiarini, G. Cerichelli, M. Capone, M. Marsili, Eur. J. Org. Chem. 2004, 623.
9. For selected examples on the halogenation of vinyl ethers see: a) G. Descotes, D. Sinou, J.-C. Martin, Bull. Soc. Chim. Fr. 1970, 10, 3730; b) E. M. Gaydou, Tetrahedron Lett. 1972, 4055; c) A. J. Duggan, S. S. Hall, J. Org. Chem., 1977, 42, 1057; d) J. R. Pfister, W. Kurz, I. T. Harrison, J. Heterocyclic Chem. 1981, 18, 831; e) G. Stork, P. M. Sher, J. Am. Chem. Soc. 1986, 108, 303; f) C. Uriel, F. Santoyo-Gonzales, Synthesis 1999, 2049; g) A. Boschi, C. Chiappe, A. De Rubertis, M. F. Ruasse, J. Org. Chem. 2000, 65, 8470; h) US Patent 6,184,394, 2003; i) L. Villo, A. Metsala, O. Parve, T. Pehk, Tetrahedron Lett. 2002, 43, 3203; j) E. Ami, S. Rajesh, J. Wang, T. Kimura, Y. Hayashi, Y. Kiso, T. Ishida, Tetrahedron Lett. 2002, 43, 2931; k) Patent WO 03/045934, 2003; l) US Patent 0153769 A1, 2003.
10. For selected examples on the halogenation of vinyl ethers see: a) G. Descotes, D. Sinou, J.-C. Martin, Bull. Soc. Chim. Fr. 1970, 10, 3730; b) E. M. Gaydou, Tetrahedron Lett. 1972, 4055; c) A. J. Duggan, S. S. Hall, J. Org. Chem., 1977, 42, 1057; d) J. R. Pfister, W. Kurz, I. T. Harrison, J. Heterocyclic Chem. 1981, 18, 831; e) G. Stork, P. M. Sher, J. Am. Chem. Soc. 1986, 108, 303; f) C. Uriel, F. Santoyo-Gonzales, Synthesis 1999, 2049; g) A. Boschi, C. Chiappe, A. De Rubertis, M. F. Ruasse, J. Org. Chem. 2000, 65, 8470; h) US Patent 6,184,394, 2003; i) L. Villo, A. Metsala, O. Parve, T. Pehk, Tetrahedron Lett. 2002, 43, 3203; j) E. Ami, S. Rajesh, J. Wang, T. Kimura, Y. Hayashi, Y. Kiso, T. Ishida, Tetrahedron Lett. 2002, 43, 2931; k) Patent WO 03/045934, 2003; l) US Patent 0153769 A1, 2003.
11. For selected examples on the halogenation of vinyl ethers see: a) G. Descotes, D. Sinou, J.-C. Martin, Bull. Soc. Chim. Fr. 1970, 10, 3730; b) E. M. Gaydou, Tetrahedron Lett. 1972, 4055; c) A. J. Duggan, S. S. Hall, J. Org. Chem., 1977, 42, 1057; d) J. R. Pfister, W. Kurz, I. T. Harrison, J. Heterocyclic Chem. 1981, 18, 831; e) G. Stork, P. M. Sher, J. Am. Chem. Soc. 1986, 108, 303; f) C. Uriel, F. Santoyo-Gonzales, Synthesis 1999, 2049; g) A. Boschi, C. Chiappe, A. De Rubertis, M. F. Ruasse, J. Org. Chem. 2000, 65, 8470; h) US Patent 6,184,394, 2003; i) L. Villo, A. Metsala, O. Parve, T. Pehk, Tetrahedron Lett. 2002, 43, 3203; j) E. Ami, S. Rajesh, J. Wang, T. Kimura, Y. Hayashi, Y. Kiso, T. Ishida, Tetrahedron Lett. 2002, 43, 2931; k) Patent WO 03/045934, 2003; l) US Patent 0153769 A1, 2003.
12. For selected examples on the halogenation of vinyl ethers see: a) G. Descotes, D. Sinou, J.-C. Martin, Bull. Soc. Chim. Fr. 1970, 10, 3730; b) E. M. Gaydou, Tetrahedron Lett. 1972, 4055; c) A. J. Duggan, S. S. Hall, J. Org. Chem., 1977, 42, 1057; d) J. R. Pfister, W. Kurz, I. T. Harrison, J. Heterocyclic Chem. 1981, 18, 831; e) G. Stork, P. M. Sher, J. Am. Chem. Soc. 1986, 108, 303; f) C. Uriel, F. Santoyo-Gonzales, Synthesis 1999, 2049; g) A. Boschi, C. Chiappe, A. De Rubertis, M. F. Ruasse, J. Org. Chem. 2000, 65, 8470; h) US Patent 6,184,394, 2003; i) L. Villo, A. Metsala, O. Parve, T. Pehk, Tetrahedron Lett. 2002, 43, 3203; j) E. Ami, S. Rajesh, J. Wang, T. Kimura, Y. Hayashi, Y. Kiso, T. Ishida, Tetrahedron Lett. 2002, 43, 2931; k) Patent WO 03/045934, 2003; l) US Patent 0153769 A1, 2003.
13. For selected examples on the halogenation of vinyl ethers see: a) G. Descotes, D. Sinou, J.-C. Martin, Bull. Soc. Chim. Fr. 1970, 10, 3730; b) E. M. Gaydou, Tetrahedron Lett. 1972, 4055; c) A. J. Duggan, S. S. Hall, J. Org. Chem., 1977, 42, 1057; d) J. R. Pfister, W. Kurz, I. T. Harrison, J. Heterocyclic Chem. 1981, 18, 831; e) G. Stork, P. M. Sher, J. Am. Chem. Soc. 1986, 108, 303; f) C. Uriel, F. Santoyo-Gonzales, Synthesis 1999, 2049; g) A. Boschi, C. Chiappe, A. De Rubertis, M. F. Ruasse, J. Org. Chem. 2000, 65, 8470; h) US Patent 6,184,394, 2003; i) L. Villo, A. Metsala, O. Parve, T. Pehk, Tetrahedron Lett. 2002, 43, 3203; j) E. Ami, S. Rajesh, J. Wang, T. Kimura, Y. Hayashi, Y. Kiso, T. Ishida, Tetrahedron Lett. 2002, 43, 2931; k) Patent WO 03/045934, 2003; l) US Patent 0153769 A1, 2003.
14. For selected examples on the halogenation of vinyl ethers see: a) G. Descotes, D. Sinou, J.-C. Martin, Bull. Soc. Chim. Fr. 1970, 10, 3730; b) E. M. Gaydou, Tetrahedron Lett. 1972, 4055; c) A. J. Duggan, S. S. Hall, J. Org. Chem., 1977, 42, 1057; d) J. R. Pfister, W. Kurz, I. T. Harrison, J. Heterocyclic Chem. 1981, 18, 831; e) G. Stork, P. M. Sher, J. Am. Chem. Soc. 1986, 108, 303; f) C. Uriel, F. Santoyo-Gonzales, Synthesis 1999, 2049; g) A. Boschi, C. Chiappe, A. De Rubertis, M. F. Ruasse, J. Org. Chem. 2000, 65, 8470; h) US Patent 6,184,394, 2003; i) L. Villo, A. Metsala, O. Parve, T. Pehk, Tetrahedron Lett. 2002, 43, 3203; j) E. Ami, S. Rajesh, J. Wang, T. Kimura, Y. Hayashi, Y. Kiso, T. Ishida, Tetrahedron Lett. 2002, 43, 2931; k) Patent WO 03/045934, 2003; l) US Patent 0153769 A1, 2003.
15. For selected examples on the halogenation of vinyl ethers see: a) G. Descotes, D. Sinou, J.-C. Martin, Bull. Soc. Chim. Fr. 1970, 10, 3730; b) E. M. Gaydou, Tetrahedron Lett. 1972, 4055; c) A. J. Duggan, S. S. Hall, J. Org. Chem., 1977, 42, 1057; d) J. R. Pfister, W. Kurz, I. T. Harrison, J. Heterocyclic Chem. 1981, 18, 831; e) G. Stork, P. M. Sher, J. Am. Chem. Soc. 1986, 108, 303; f) C. Uriel, F. Santoyo-Gonzales, Synthesis 1999, 2049; g) A. Boschi, C. Chiappe, A. De Rubertis, M. F. Ruasse, J. Org. Chem. 2000, 65, 8470; h) US Patent 6,184,394, 2003; i) L. Villo, A. Metsala, O. Parve, T. Pehk, Tetrahedron Lett. 2002, 43, 3203; j) E. Ami, S. Rajesh, J. Wang, T. Kimura, Y. Hayashi, Y. Kiso, T. Ishida, Tetrahedron Lett. 2002, 43, 2931; k) Patent WO 03/045934, 2003; l) US Patent 0153769 A1, 2003.
16. For selected examples on the halogenation of vinyl ethers see: a) G. Descotes, D. Sinou, J.-C. Martin, Bull. Soc. Chim. Fr. 1970, 10, 3730; b) E. M. Gaydou, Tetrahedron Lett. 1972, 4055; c) A. J. Duggan, S. S. Hall, J. Org. Chem., 1977, 42, 1057; d) J. R. Pfister, W. Kurz, I. T. Harrison, J. Heterocyclic Chem. 1981, 18, 831; e) G. Stork, P. M. Sher, J. Am. Chem. Soc. 1986, 108, 303; f) C. Uriel, F. Santoyo-Gonzales, Synthesis 1999, 2049; g) A. Boschi, C. Chiappe, A. De Rubertis, M. F. Ruasse, J. Org. Chem. 2000, 65, 8470; h) US Patent 6,184,394, 2003; i) L. Villo, A. Metsala, O. Parve, T. Pehk, Tetrahedron Lett. 2002, 43, 3203; j) E. Ami, S. Rajesh, J. Wang, T. Kimura, Y. Hayashi, Y. Kiso, T. Ishida, Tetrahedron Lett. 2002, 43, 2931; k) Patent WO 03/045934, 2003; l) US Patent 0153769 A1, 2003.
17. For selected examples on the halogenation of vinyl ethers see: a) G. Descotes, D. Sinou, J.-C. Martin, Bull. Soc. Chim. Fr. 1970, 10, 3730; b) E. M. Gaydou, Tetrahedron Lett. 1972, 4055; c) A. J. Duggan, S. S. Hall, J. Org. Chem., 1977, 42, 1057; d) J. R. Pfister, W. Kurz, I. T. Harrison, J. Heterocyclic Chem. 1981, 18, 831; e) G. Stork, P. M. Sher, J. Am. Chem. Soc. 1986, 108, 303; f) C. Uriel, F. Santoyo-Gonzales, Synthesis 1999, 2049; g) A. Boschi, C. Chiappe, A. De Rubertis, M. F. Ruasse, J. Org. Chem. 2000, 65, 8470; h) US Patent 6,184,394, 2003; i) L. Villo, A. Metsala, O. Parve, T. Pehk, Tetrahedron Lett. 2002, 43, 3203; j) E. Ami, S. Rajesh, J. Wang, T. Kimura, Y. Hayashi, Y. Kiso, T. Ishida, Tetrahedron Lett. 2002, 43, 2931; k) Patent WO 03/045934, 2003; l) US Patent 0153769 A1, 2003.
18. For selected examples on the halogenation of vinyl ethers see: a) G. Descotes, D. Sinou, J.-C. Martin, Bull. Soc. Chim. Fr. 1970, 10, 3730; b) E. M. Gaydou, Tetrahedron Lett. 1972, 4055; c) A. J. Duggan, S. S. Hall, J. Org. Chem., 1977, 42, 1057; d) J. R. Pfister, W. Kurz, I. T. Harrison, J. Heterocyclic Chem. 1981, 18, 831; e) G. Stork, P. M. Sher, J. Am. Chem. Soc. 1986, 108, 303; f) C. Uriel, F. Santoyo-Gonzales, Synthesis 1999, 2049; g) A. Boschi, C. Chiappe, A. De Rubertis, M. F. Ruasse, J. Org. Chem. 2000, 65, 8470; h) US Patent 6,184,394, 2003; i) L. Villo, A. Metsala, O. Parve, T. Pehk, Tetrahedron Lett. 2002, 43, 3203; j) E. Ami, S. Rajesh, J. Wang, T. Kimura, Y. Hayashi, Y. Kiso, T. Ishida, Tetrahedron Lett. 2002, 43, 2931; k) Patent WO 03/045934, 2003; l) US Patent 0153769 A1, 2003.
19. For selected examples on the halogenation of vinyl ethers see: a) G. Descotes, D. Sinou, J.-C. Martin, Bull. Soc. Chim. Fr. 1970, 10, 3730; b) E. M. Gaydou, Tetrahedron Lett. 1972, 4055; c) A. J. Duggan, S. S. Hall, J. Org. Chem., 1977, 42, 1057; d) J. R. Pfister, W. Kurz, I. T. Harrison, J. Heterocyclic Chem. 1981, 18, 831; e) G. Stork, P. M. Sher, J. Am. Chem. Soc. 1986, 108, 303; f) C. Uriel, F. Santoyo-Gonzales, Synthesis 1999, 2049; g) A. Boschi, C. Chiappe, A. De Rubertis, M. F. Ruasse, J. Org. Chem. 2000, 65, 8470; h) US Patent 6,184,394, 2003; i) L. Villo, A. Metsala, O. Parve, T. Pehk, Tetrahedron Lett. 2002, 43, 3203; j) E. Ami, S. Rajesh, J. Wang, T. Kimura, Y. Hayashi, Y. Kiso, T. Ishida, Tetrahedron Lett. 2002, 43, 2931; k) Patent WO 03/045934, 2003; l) US Patent 0153769 A1, 2003.
20. For selected examples on the halogenation of vinyl ethers see: a) G. Descotes, D. Sinou, J.-C. Martin, Bull. Soc. Chim. Fr. 1970, 10, 3730; b) E. M. Gaydou, Tetrahedron Lett. 1972, 4055; c) A. J. Duggan, S. S. Hall, J. Org. Chem., 1977, 42, 1057; d) J. R. Pfister, W. Kurz, I. T. Harrison, J. Heterocyclic Chem. 1981, 18, 831; e) G. Stork, P. M. Sher, J. Am. Chem. Soc. 1986, 108, 303; f) C. Uriel, F. Santoyo-Gonzales, Synthesis 1999, 2049; g) A. Boschi, C. Chiappe, A. De Rubertis, M. F. Ruasse, J. Org. Chem. 2000, 65, 8470; h) US Patent 6,184,394, 2003; i) L. Villo, A. Metsala, O. Parve, T. Pehk, Tetrahedron Lett. 2002, 43, 3203; j) E. Ami, S. Rajesh, J. Wang, T. Kimura, Y. Hayashi, Y. Kiso, T. Ishida, Tetrahedron Lett. 2002, 43, 2931; k) Patent WO 03/045934, 2003; l) US Patent 0153769 A1, 2003.
21. a) F. Goodridge, S. Harrison, R. E. Plimley, J. Electroanal. Chem. 1986, 214, 283;
22. b) R. I. Kruglikova, L. N. Kralinina, Khimiya Geterotsiklicheskikh Soedinenii 19 72, 7, 875;
23. c) S. Torii, H. Uneyama, H. Tanaka, T. Yamanaka, T. Yasuda, M. Ono, Y. Kohmoto, J. Org. Chem. 19 81, 46, 3312.
24. H. Masuda, K. Takase, M. Nishio, A. Hasegawa, Y. Nishiyama, Y. Ishii, J. Org. Chem. 1994, 59, 5550.
25. a) A. Butler, J. V. Walker, Chem. Rev. 1993, 93, 1937;
26. b) M. C. R. Franssen, Catal. Today 1994, 22, 441;
27. c) S. Aoun, M. Baboulène, J. Mol. Catal. B: Enzymatic 1998, 4, 101;
28. for examples on enzymatic halohydration of glycols, see: d) K. Liu, C.-H. Wong, J. Org. Chem. 1992, 57, 3748; e) H. Fu, H. Kondo, Y. Ichikawa, G. C. Look, C.-H. Wong, J. Org. Chem. 1992, 57, 7265.
29. for examples on enzymatic halohydration of glycols, see: d) K. Liu, C.-H. Wong, J. Org. Chem. 1992, 57, 3748; e) H. Fu, H. Kondo, Y. Ichikawa, G. C. Look, C.-H. Wong, J. Org. Chem. 1992, 57, 7265.
30. a) B. Sels, D. De Vos, M. Buntinx, F. Pierard, F. Kirsch-De Mesmaeker, P. Jacobs, Nature 1999, 400, 855 and references cited therein;
31. b) B. Sels, D. De Vos, P. Jacobs, J. Am Chem. Soc. 2001, 123, 8350;
32. c) B. Sels, D. De Vos, M. Buntinx, P. Jacobs, J. Catal. 2003, 216, 288;
33. d) R. Ben-Daniel, S. P. de Visser, S. Shaik, R. Neumann. J. Am. Chem. Soc. 2003, 125, 12116;
34. e) B. M. Choudary, T. Someshwar, Ch. Venkat Reddy, M. Lakshmi Kantam, K. Jeeva Ratnam, L. V. Sivaji, Applied Catal. A: General 2003, 251, 397.
35. a) B. Sels, D. De Vos, P. Jacobs, Catalysis Rev. 2001, 43, 443;
36. b) D. De Vos, B. Sels, P. Jacobs, Cattech 2002, 6, 14;
37. c) B. M. Choudary, N. S. Chowdari, S. Madhi, M. L. Kantam, J. Org. Chem. 2003, 68, 1736;
38. d) B. M. Choudary, S. Madhi, N. S. Chowdari, M. L. Kantam, B. Sreedhar, J. Am. Chem. Soc. 2002, 124, 14127.
39. a) S. J. Danishefsy, M. T. Bilodeau, Angew. Chem. Int. Ed. Engl. 1996, 35, 1380;
40. b) D. Horton, W. Priebe, O. Varela. J. Org. Chem. 1986, 51, 3479;
41. c) R. W. Friesen, S. J. Danishefsky, J. Am. Chem. Soc. 1989, 111, 6656;
42. d) C.-H. Yang, J.-S. Wu, W.-B. Ho, Tetrahedron 1990, 46, 4205;
43. e) C. H. Marzabadi, C. D. Spilling, J. Org. Chem. 1993, 58, 3761;
44. f) C. H. Marzabadi, C. D. Spilling, L. M. Tyler, Tetrahedron 1994, 50, 6783;
45. g) G. V. M. Sharma, K. Krishnudu, S. M. Rao, Tetrahedron: Asymmetry 199 5, 6, 543;
46. h) A. Kirschning, Eur. J. Org. Chem. 1998, 2267;
47. H. G. Bazin, M. W. Wolff, R. J. Linhardt, J. Org. Chem. 1999, 64, 144;
48. j) G. B. Kok, T. Phan, M. von Itzstein, J. Carbohydr. Chem. 2001, 20, 359.
49. a) R. G. Doshin, S. J. Danishefsky, J. Am. Chem. Soc. 199 2, 114, 3471;
50. b) C. Ernst, M. Piacenza, S. Grimme, W. Klaffke, Carbohydr. Res. 2003, 338, 231;
51. c) X.-Q. Yu, J.-S. Huang, W.-Y. Yu, C.-M. Che, J. Am. Chem. Soc. 2000, 122, 5337;
52. d) F. P. Boulineau, A. Wei, Org. Lett. 2002, 4, 2281.
53. M. F. Ruasse, G. L. Moro, R. B. Galland, C. Chiappe, G. Bellucci, J. Am. Chem. Soc. 1997, 119, 12492.
54. a) B. Sels, D. De Vos, P. Grobet, F. Pierard, F. Kirsch-De Mesmaeker, P. Jacobs, J. Phys. Chem. B 1999, 103, 11114;
55. b) F. Cavani, F. Trifirò, A. Vaccari, Catal. Today 1991, 11, 173 and references cited therein.
56. a) K. Tatsuta, K. Fujimato, M. Kinoshita, Carbohydr. Res. 1977, 54, 85;
57. b) J. S. Kozlowski, C. H. Marzabadi, N. P. Rath, C. D. Spilling, Carbohydr. Res. 1997, 300, 301;
58. c) D. Horton, W. Priebe, M. Sznaidman, Carbohydr. Res. 1990, 205, 71;
59. d) A. R. De Corso, B. Panunzi, M. Tingoli, Tetrahedron Lett. 2001, 42, 7245.
60. a) C. Monneret, P. Choay, Carbohydr. Res. 1981, 96, 299;
61. b) C. H. Marzabadi, C. D. Spilling, J. Org. Chem. 1993, 58, 3761;
62. c) P. J. Garegg, B. Samuelsson, J. Chem. Soc. Perkin Trans. 1, 1980, 2866.