Mild and efficient method for the cleavage of benzylidene acetals by using erbium (III) triflate

Organic and Biomolecular Chemistry

Volumn 3, Issue 22, 2005, Pages 4129-4133

  Procopio, Antonio ^a   Dalpozzo, Renato ^b   De Nino, Antonio ^b   Maiuolo, Loredana ^b   Nardi, Monica ^b   Romeo, Giovanni ^c  

^a UNIVERSITY MAGNA GRAECIA OF CATANZARO   (Italy)

^b UNIVERSITY OF CALABRIA   (Italy)

^c UNIVERSITY OF MESSINA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; DERIVATIVES; ERBIUM; REACTION KINETICS; SOLVENTS;

ACETIC ANHYDRIDES; BENZYLIDENE ACETALS;

ACETAL RESINS;

ARTICLE;

EID: 28444452301     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b511314h     Document Type: Article

References (63)

1. (a) T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, 3rd edn., John Wiley and Sons, New York, 1999;
2. (b) P. J. Kocienski, Protecting Groups, 1st edn, George Thieme Verlag, Stuttgart, 1994;
3. (c) P. J. Kocienski, J. Chem. Soc., Perkin Trans. 1, 2001, 2109-2135.
4. Preparative Carbohydrate Chemistry, ed. S. Hanessian, Marcel Dekker Inc., New York, 1997, pp. 53-67.
5. (a) M. P. DeNinno, J. B. Etienne and K. C. Duplantier, Tetrahedron Lett., 1995, 36, 669-672;
6. (b) N. L. Pohl and L. L. Kiessling, Tetrahedron Lett., 1997, 38, 6985-6988;
7. (c) J. Lu and T.-H. Chan, Tetrahedron Lett., 1998, 39, 355-358;
8. (d) H. Kotsuki, Y. Ushio, N. Yoshimura and M. Ochi, J. Org. Chem., 1987, 52, 2594-2596;
9. (e) A. Arasappan and B. Fraser-Reid, J. Org. Chem., 1996, 61, 2501-2506;
10. (f) C. W. Andrews, R. Rodebaugh and B. Fraser-Reid, J. Org. Chem., 1996, 61, 5280-5289.
11. (a) L. Qiao and J. C. Vederas, J. Org. Chem., 1993, 58, 3480-3482;
12. (b) B. Mukhopadhyay and N. Roy, Carbohydr. Res., 2003, 338, 589-596;
13. (c) H. Tanaka, T. Amaya and T. Takahashi, Tetrahedron Lett., 2003, 44, 3053-3057;
14. (d) Y. Vera-Ayoso, P. Borrachero, Cabrera-Escribano, A. T. Carmona and M. Gómez-Guillén, Tetrahedron: Asymmetry, 2004, 15, 429-444;
15. (e) P. H. G. Wiegerinck, L. Fluks, J. B. Hammink, S. J. E. Mulders, F. M. H. de Groot, H. L. M. van Rozendaal and H. W. Scheeren, J. Org. Chem., 1996, 61, 7092-7100;
16. (f) B. Delpech, D. Calvo and R. Lett, Tetrahedron Lett., 1996, 37, 1015-1018;
17. (g) P. Meresse, C. Monneret and E. Bertounesque, Tetrahedron, 2004, 60, 2657-2671.
18. (a) T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, 3rd edn, John Wiley and Sons, New York, 1999, pp. 217-222;
19. (b) P. J. Kocienski, Protecting Groups, 1st edn, George Thieme Verlag, Stuttgart, 1994, pp. 96-102.
20. P. Meresse, C. Monneret and E. Bertounesque, Tetrahedron, 2004, 60, 2657-2671.
21. B. Mukhopadhyay and N. Roy, Carbohydr. Res., 2003, 338, 589-596.
22. M. Smith, D. H. Rammler, I. H. Goldberg and H. G. Khorana, J. Am. Chem. Soc., 1962, 84, 430-440.
23. U. Ellervik, Tetrahedron Lett., 2003, 44, 2279-2281.
24. (a) G. Bartoli, G. Cupone, R. Dalpozzo, A. De Nino, L. Maiuolo, E. Marcantoni and A. Procopio, SYNLETT, 2001, 12, 1897-1900;
25. (b) G. Bartoli, G. Cupone, R. Dalpozzo, A. De Nino, L. Maiuolo, A. Procopio, L. Sambri and A. Tagarelli, Tetrahedron Lett., 2002, 43, 5945-5947;
26. (c) R. Dalpozzo, A. De Nino, L. Maiuolo, A. Procopio, A. Tagarelli, G. Sindona and G. Bartoli, J. Org. Chem., 2002, 67, 9093-9095;
27. (d) R. Dalpozzo, A. De Nino, L. Maiuolo, A. Procopio, M. Nardi, G. Bartoli and R. Romeo. Tetrahedron Lett., 2003, 44, 5621-5624;
28. (e) G. Bartoli, M. Bosco, R. Dalpozzo, E. Marcantoni, M. Massaccesi, S. Rivalsi and L. Sambri, SYNLETT, 2003, 1, 39-42;
29. (f) R. Dalpozzo, A. De Nino, L. Maiuolo, M. Nardi, A. Procopio and Tagarelli, Synthesis, 2004, 496-498;
30. (g) A. Procopio, R. Dalpozzo, A. De Nino, M. Nardi, G. Sindona and A. Tagarelli, SYNLETT, 2004, 14, 2633-2635;
31. (h) R. Dalpozzo, A. De Nino, L. Maiuolo, M. Nardi, A. Procopio and A. Tagarelli, Adv. Synth. Catal., 2004, 346, 1465-1470;
32. (i) A. Procopio, R. Dalpozzo, A. De Nino, L. Maiuolo, M. Nardi and B. Russo, Adv. Synth. Catal., 2005, DOI: 10.1002/adsc.200505096.
33. (a) E. Messems, M. Van Montagu, A. de Bruyn and A. W. H. Jans, Carbohydr. Res., 1989, 186, 241-253;
34. (b) N. Rehnberg and G. Magnusson, J. Org. Chem., 1990, 55, 5467-5476;
35. (c) C. Andre, P. Luger, R. Bach and J.-H. Fuhrhop, Carbohydr. Res., 1995, 266, 15-35;
36. (d) J. Kitajima, T. Ishikawa, Y. Tanaka and Y. Ida, Chem. Pharm. Bull., 1999, 47, 988-992;
37. (e) A. V. Bogatsky, N. G. Lukyanenko, A. V. Lobach, N. Yu. Nazarova and L. P. Karpenko, Synthesis, 1984, 2, 139-140;
38. (f) S. H. Khan, K. J. Rakesh and L. M. Kheushi, Carbohydr. Res., 1990, 207, 57-64;
39. (g) R. Eby, K. T. Webster and C. Shuerch, Carbohydr. Res., 1994, 129, 111-120;
40. (h) S. Furniss, A. J. Hannaford, P. W. G. Smith and A. R. Tatchell, Vogel's: Textbook of Practical Organic Chemistry, pp. 658-663;
41. (i) P. Ramesh, V. L. N. Reddy, D. Venugopal, M. Subrahmanyam and Y. Venkateswarlu, Synth. Commun., 2001, 31, 2599-2604;
42. (f) M. Adinolfi, L. De Napoli, G. Di Fabio, A. Iadonisi, D. Montesarchio and G. Piccialli, Tetrahedron, 2002, 58, 6697-6704;
43. (k) W. J. Goux and C. J. Unkefer, Carbohydr. Res., 1987, 159, 191-210;
44. (l) N. Ikamoto, O. K. Kim, C. L. Lo, V. Satyanarayama, M. Chang and K. Nakanishi, Tetrahedron Lett., 1992, 33, 4295-4298;
45. (m) C. M. McCloskey and G. H. Coleman, J. Org. Chem., 1945, 10, 184-193;
46. (n) M. Matsui and M. Okada, Chem. Pharm. Bull., 1970, 18, 2129-2132;
47. (o) A. Numata, C. Takahashi, R. Fujiki, E. Kitano, A. Kitajima and T. Takemura, Chem. Pharm. Bull., 1990, 38, 2862;
48. (p) S. Jeganathan and P. Vogel, J. Org. Chem., 1991, 56, 1133-1142.
49. 3 was confirmed by comparison with the IR spectrum of commercial product. (KBr): 511 (47.431); 586 (43.79); 648 (24.23); 1017 (18.56); 1319 (7.60); 2964 (7.91).
50. (a) P. Ramesh, V. L. N. Reddy, D. Venugopal, M. Subrahmanyam and Y. Venkateswarlu, Synth. Commun., 2001, 31, 2599-2604;
51. (b) M. Adinolfi, L. De Napoli, G. Di Fabio, A. Iadonisi, D. Montesarchio and G. Piccialli, Tetrahedron, 2002, 58, 6697-6704;
52. (c) W. J. Goux and C. J. Unkefer, Carbohydr. Res., 1987, 159, 191-210;
53. (d) N. Ikamoto, O. K. Kim, C. L. Lo, V. Satyanarayama, M. Chang and K. Nakanishi, Tetrahedron Lett., 1992, 33, 4295-4298;
54. (e) C. M. Me Closkey and G. H. Coleman, J. Org. Chem., 1945, 10, 184-193;
55. (f) M. Matsui and M. Okada, Chem. Pharm. Bull., 1970, 18, 2129-2132;
56. (g) A. Numata, C. Takahashi, R. Fujiki, E. Kitano, A. Kitajima and T. Takemura, Chem. Pharm. Bull., 1990, 38, 2862;
57. (h) S. Jeganathan and P. Vogel, J. Org. Chem., 1991, 56, 1133-1142.
58. (a) P. T. Anastas and J. C. Warner, Green Chemistry: Theory and Practice, Oxford Science Publications, Oxford, 1998;
59. (b) T. C. Collins, Green Chemistry: Frontiers in Chemical Synthesis and Processes, Oxford University Press, Oxford, 1998;
60. (c) P. Tundo, P. Anastas StC., D. Black, J. Breen, T. Collins, S. Memoli, J. Miyamoto, M. Polyakoff and W. Tumas, Pure Appl. Chem., 2000, 72, 1207;
61. (d) P. T. Anastas and M. M. Kirchhoff, Acc. Chem. Res., 2002, 35, 68.
62. (a) F. W. Lichtenthaler, W. Eberhard and S. Braun, Tetrahedron Lett., 1981, 22, 4401-4404;
63. (b) E. C. Garrett and A. S. Serianni, Carbohydr. Res., 1990, 208, 23-35.