A study of Pd(II) Cl2/CuCl catalysed Wacker reaction for the deprotection of prop-2-enyl and prop-1-enyl ethers

Tetrahedron

Volumn 53, Issue 51, 1997, Pages 17501-17512

  Mereyala, Hari Babu ^a   Lingannagaru, Sarita Reddy ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL ETHER; GLYCOPYRANOSIDE; PALLADIUM COMPLEX;

ARTICLE; CATALYSIS; CHEMICAL REACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0030823018     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10198-3     Document Type: Article

References (73)

1. (a) Philips, F.C. Am. Chem. J. 1894, 16, 255.
2. (b) Smidt, J.; Hafner, W.; Jira, R.; Sedlmeier, J.; Sieber, R.; Ruttinger, R and Kojer, H. Angew. Chem. 1959, 71, 176.
3. (c) Smidt, J.; Hafner, W.; Jira, R and Sedlmeier, J. Angew. Chem. Int. Ed. 1962, 1, 80.
4. (d) Hafner, W.; Jira, R.; Sedlmeier, J and Smidt, J. Chem. Ber. 1962, 95, 7575.
5. (e) Jira, R.; Sedlmeier, J and Smidt, J. Liebigs. Ann. Chem. 1966, 693, 99.
6. (a) Patrick, M and Henry. 'Palladium catalysed oxidation of hydrocarbons'; D. Reidel Publishing Company : Holland. 1928.
7. (b) Tsuji, J. Synthesis. 1984, 369.
8. (c) Tsuji, J.; Nagashima, H and Nemoto. H. Org. Synthesis. 1984, 62, 9.
9. (d) Heck, R.F. in 'Palladium Reagents in Organic Syntheses' Academic Press; London. 1985, 59.
10. Alandis, N.; Rieo, I,; Condere, F.; Perez, E and Lattis, A. Arab Gulf J. Sci. Res., 1989, 7, 1.
11. Tang, H.; Sherrington, G and David, C. Polymer 1993, 34, 2821.
12. Inokuchi, T.; Ping, L.; Fumihiro, H.; Miyoko, I and Sigeru, T. Chem. Lett., 1994, 111, 121.
13. (a) Tsuji, J.; Kaito, M and Takahashi, T. Bull. Chem. Soc. Japan. 1978, 51, 547.
14. (b) Tsuji, J.; Kaito, M.; Yamamda, T and Mandai, T. Bull. Chem. Soc. Japan. 1978, 51, 1915.
15. (c) Hase, T.A and McCoy, K. Synth. Commun., 1979, 9, 63.
16. (d) Subramaniam, C.S.; Thomas,P.J.; Mamdapur, V . R and Chadha, M.S. Synthesis. 1978, 468.
17. (a) Bose, A.K.; Krishnan, L.; Wagle, D.R. and Manhas, M.S. Tetrahedron Letters. 1986, 27, 5955.
18. (b) Hosokawa, T.; Ohta, T.; Kanayama, S and Shun-Ichi, M. J. Org. Chem. 1987, 52, 1758.
19. (c) Nokami, J.; Ogawa, H.; Miyamato, S.; Mandai, T.; Wakabayashi, S and Tsuji, J. Tetrahedron Letters. 1988, 29, 5181.
20. (d) Pellissier, H.; Michellys, P.Y. and Santelli, M. Tetrahedron Letters. 1994, 35, 6481.
21. (e) Kang, S.-K.; Jung, K.-Y.; Chung, J.-U.; Namkoong, E.-Y and Kim, T.-H. J. Org. Chem. 1995, 60, 4678.
22. Reddy, K.K.; Palakodety, R.K. and Mereyala, H.B. Tetrahedron Letters. 1996, 37, 6007.
23. Gadikota, R.K and Mereyala, H.B. J.C.S. Perkin Trans 1. communicated. 1997.
24. Cunningham, J.; Gigg, R and Warren, C.D. Tetrahedron Letters. 1964, 1191.
25. (a) Corey, E.J and Suggs, J.W. J. Org. Chem. 1973, 38, 3224.
26. (b) Gent, P.A and Gigg, R. J. Chem. Soc. Chem. Comm., 1974, 227.
27. Oltvoort, J.J.; Van Boeckel, C.A.; de Konig, J.H and Van Boom, J.H. Synthesis, 1981, 305.
28. Gigg, R and Warren, C.D. J. Chem. Soc., (c) 1968, 1903.
29. Nashed, M.A and Anderson, L.J. Chem. Soc. Chem. Comm., 1982, 1274,.
30. Boss, R and Scheffold, R. Angew. Chem. 1976, 88, 558.
31. Kariyone, K and Yazawa, H. Tetrahedron Letters. 1970, 34, 2885.
32. (a) Ogawa, T. Nakabayashi, S and Kitazima, T. Carbohydr. Res., 1983, 114, 225.
33. (b) Kloosterman, M.; Van Boom, J.H and Chetelard, D. Tetrahedron Letters. 1985, 41, 5045.
34. Nakayama, K.; Voto, K.; Higashi, K.; Soga, T and Kusama, T. Chem. Pharm. Bull., 1992, 40, 1718.
35. Espanet, B.; Dunach, E and Perichon, J. Tetrahedron Letters. 1992, 33, 2485.
36. Akiyama, T.; Hirofuji, H and Ozaki, S. Bull. Chem. Soc. Japan. 1992, 65, 1932.
37. Diaz, R.R.; Melgarejo, C.R.; Maria, T.P.L.E and Cubero, I.I. J. Org. Chem. 1994, 59, 7928.
38. Hisanka, I.; Taguchi, T and Hanzawa, Y. J. Org. Chem. 1993, 58, 774.
39. Luning, J.; Mollu, U.; Debski, N and Welzel, P. Tetrahedron Letters. 1993, 34, 5871.
40. Bieg, T and Szega, W. J. Carbohydr. Chem., 1985, 4, 441.
41. (a) Desmurs, J and Lecouve, P.J. Eur. Pat. Appl. EP.378,463 (Chem.Abstr., 114:P101333p) 1990.
42. (b) Lin, I.J.B and Jong, S.J. U.S. 5,068,458 (Chem.Abstr. 117:P111253p) 1991.
43. (c) Narayanan, K.S.; Plotkin, J.S.; Vara, F.J.; Dougherty, J.A.; Miller, M.M and Taylor, P.D.PCT Int. Appl. . WO.9,204,383, US Appl. 579,512 (Chem.Abstr. P173455q) 1992.
44. Kanayama, K and Ichikawa, S.Kokai Tokkyo Koho JP o5,383(9317.383) (Chem.Abstr. 118: P254531j) 1991.
45. Ogawa, T and Ito, Y. J. Am. Chem. Soc., 1997, 119, 5562.
46. (a) Lakhmiri, R.; Lhoste, P.; Kryczka, B and Sinon, D.J. Carbohydr. Chem., 1993, 12, 223.
47. (b) Lakhmiri, R and Lhoste, P. Tetrahedron Letters. 1989, 30, 4669.
48. Mereyala, H.B and Guntha, S. Tetrahedron Letters. 1993, 34, 6929.
49. Ragupathi, O.; Park, T.K.; Zhang, S.; Kim, I.J.; Graber, L.; Adlur, S.; Lloyd, K.O.; Danishefshy, S.J and Livingston, P.O. Angew. Chem. 1997, 36, 125.
50. Tronchet, J.M.J.; Zsely, M and Geoffroy, M. Carbohydr. Res., 1995, 1, 245.
51. Rodebaugh, R and Fraser-Reid, B. Tetrahedron, 1996, 52, 7663.
52. (a) Paulsen, H and Sumfleth, B. Chem. Ber., 1979, 112, 3203.
53. (b) Koto, S.; Morishima, N.; Miyata, Y and Zen, S. Bull. Chem. Soc. Japan. 1976, 49, 2639.
54. McQuillin, F.J and Parker, D.D. J. Chem. Soc., Perkin Trans 1, 1974, 809.
55. Mabbott, D.J.; Mann, B.E and Martlis, P.M. J. Chem. Soc. Dalton 1977, 294.
56. (a) Papadmitrion, V and Paraskewas, S. Chem. Ztg., 1975, 99, 495.(Chem.Abstr.84:90281)
57. (b) Papadmitrion, V.; Paraskewas, S and Danoponlos, M.Chem. Ztg., 1980, 104, 238.(Chem.Abstr. 94:102769r)
58. (c) Clark, H.C.; Smith,M.J.H and Rugger, H. Organometallics, 1988, 10, 2085.
59. Rajan Babu, T.V.; Fukumaga, T and Reddy, G.S. J. Am. Chem. Soc., 1989, 111, 1759.
60. Mereyala, H.B and Gurrala, S.R. Carbohydr. Res., 1997, manuscript communicated.
61. (a) Glandemans, C.P.J and Fletcher, Jr. H.G. Methods in Carbohydr. Chem., 1972, 6, 373.
62. (b) Dejter-Juszynski, M and Flowers, H.M. Carbohydr. Res., 1971, 18, 219.
63. Fraser Reid, B.; Konradsson, P.; Mottoo, D.R.; Udodong, U. J. Chem. Soc. Chem. Commun., 1988, 823.
64. Veenemann, G.H and Van Boom, J.H. Tetrahedron Letters. 1990, 31, 275.
65. Mereyala, H.B and Reddy, G.V. Tetrahedron. 1991, 47, 9721.
66. Kuster, J.M and Dyong, J. Leibigs Ann. Chem., 1975, 12, 2179.
67. Nelson, K and Richtmyer. Methods in Carbohydr. Chem., 1962, 1, 107.
68. Finch, P.; Iskander, G.H and Siriwardena, A.H. Carbohydr. Res., 1991, 210, 319.
69. Schmidt, O.T. Methods in Carbohydr. Chem., 1963, 2, 319.
70. Shafizadeh, F. Methods in Carbohydr. Chem., 1962, 1, 193.
71. (a) Schmidt, O.T. Methods in Carbohydr. Chem., 1963, 2, 318.
72. (b) Hall, L.D.Carbohydr. Res., 1976, 47, 299.
73. Mully, V.M.; Zsindely, J and Schmid, Hans. Helv. Chem. Acta. 1975, 58, 610.