Efficient and selective cleavage of silyl ethers with antimony trichloride

Letters in Organic Chemistry

Volumn 3, Issue 1, 2006, Pages 13-15

  Wu, Qinpei ^a   Wang, Yuan ^a   Chen, Wei ^a   Wang, Hao ^a   Liu, Hua ^a  

^a BEIJING INSTITUTE OF TECHNOLOGY   (China)

Author keywords

Antimony; Catalysis; Desilylation; Hydrolyses; Protecting groups; Silyl ethers

Indexed keywords

EID: 34247223575     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017806774964413     Document Type: Article

References (52)

1. (a) Greene, T. W.; Wuts, P. G. Protective groups in Organic Synthesis, 2nd ed.; John Wiley and Sons: New York, 1999;
2. (b) Kocienski, P. J.; Protecting Groups; Georg Thieme-Stuttgart: New York, 2004.
3. Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190.
4. Bora, U.; Bose, G.; Chaudhuri, M. K.; Dhar, S. S.; Gopinath, R.; Khan, R.; Patel, B. K. Org. Lett. 2000, 2, 247.
5. Reese, C. B.; Wu, Q. Org. Biomol. Chem. 2003, 1, 3160.
6. (a) Ranu, B. C.; Jana, U.; Majee, A. Tetrahedron Lett. 1999, 40, 1985;
7. (b) Metcalf, B. W.; Burkhart, J. P.; Jund, K. Tetrahedron Lett. 1980, 21, 35.
8. (a) Paquette, L. A.; Doherty, A. M.; Rayner, C. M. J. Am. Chem. Soc. 1992, 11, 3910;
9. (b) Toshima, T.; Tatsuta, K.; Kinoshita, M. Bull. Chem. Soc. Jpn. 1988, 61, 2396.
10. Newton, R. F.; Reynolds, D. P.; Finch, M. A. W.; Kelly, D. R.; Roberts, S. M. Tetrahedron Lett. 1979, 20, 3981.
11. (a) Masamune, S.; Lu, L. D.-L.; Jackson, W. P.; Kaiho, T.; Toyoda, T. J. Am. Chem. Soc. 1982, 104, 5523;
12. (b) Chen, C. T.; Chao, S.-D.; Ten, K.-C.; Chen, C.-H.; Chou, I.-C.; Hon, S.-W. J. Am. Chem. Soc. 1997, 119, 11341;
13. (c) Nicolaou, K. C.; Finlay, M. R. V.; Ninkovic, S.; Sarabia, F. Tetrahedron, 1998, 54, 7127;
14. (d) Baker, R.; Cummings, W. J.; Hayes, J. F.; Kumar, A. J. Chem. Soc. Chem. Commun. 1986, 1237.
15. Thomas, E. J.; Williams, A. C. J. Chem. Soc. Chem. Commun. 1987, 992.
16. (a) Kawahara, S.; Wada, T.; Sekine, M. J. Am. Chem. Soc. 1996 118, 9461;
17. (b) Durand, J.; Larcheveque, M.; Petit, Y. Tetrahedron lett. 1998, 39, 5743.
18. Iimura, S.; Manabe, K.; Kobayashi, S. J. Org. Chem. 2003, 68, 8723.
19. (a) Yadav, J. S.; Reddy, B. V. S.; Madan, C. New J. Chem. 2000, 24, 853;
20. (b) Oriyama, T.; Kobayashi, Y.; Noda, K. Synlett, 1998, 1047;
21. (c) Bartoli G.; Cupone, G.; Dalpozzo, R.; De Nino, A.; Maiuolo, L.; Procopio, A.; Sambri, L.; Tararelli, A. Tetrahedron Lett. 2002, 43, 5945;
22. (d) Bartoli, G.; Bosco, M.; Marcantoni, E.; Sambri, L.; Torregiani, E. Synlett, 1998, 209;
23. (e) Bajwa, J. S.; Vivelo, J.; Slade, J.; Repic, O.; Blacklock, T. Tetrahedron Lett. 2000, 41, 6021;
24. (f) Crouch, R. D.; Romany, C. A.; Kreshock, A. C.; Menconi, K. A.; Zile, J. L. Tetrahedron Lett. 2004, 45, 1279;
25. (g) Yang, Y.; Yang, W.; Teo, C.; Lin, C. Synlett, 2000, 1634.
26. (a) Tanemura, K.; Suzuki, T.; Horaguchi, T. J. Chem. Soc. Perkin Trans. 1, 1992, 2997;
27. (b) DattaGupta, A.; Singh, R.; Singh, V. K. Synlett, 1996, 69;
28. (c) Vaino, A. R.; Szarek, W. A. J. Chem. Soc., Chem. Commun. 1996, 2351;
29. (d) Wang, M.; Li, C.; Yin, D.; Liang, X.-T. Tetrahedron Lett. 2002, 43, 8727;
30. (e) Ikawa, T.; Hattori, K.; Sajiki, H.; Hirota, K. Tetrahedron, 2004, 60, 6901;
31. (f) Corey, E. J.; Jones, G. B. J. Org. Chem. 1992, 57, 1028;
32. (g) Lipshutz, B. H.; Keith, J. Tetrahedron Lett. 1998, 39, 2495;
33. (h) Ikawa, T.; Sajiki, H.; Hirota, K. Tetrahedron, 2004, 60, 6189.
34. Wu, Q.; Simons, C. Synthesis, 2004, 10, 1533.
35. Norcross, R. D.; Paterson, I. Chem. Rev. 1995, 95, 2041.
36. Zhu, X.; Williams, H. J.; Scott, A. I. J. Chem. Soc. Perkin Trans. 1, 2000, 2305.
37. Grieco, P. A.; Markworth, C. J. Tetrahedron Lett. 1999, 40, 665.
38. Lee, A. S.; Yeh, H.; Tsai, M. Tetrahedron Lett. 1995, 36, 6891.
39. Crouch, R. D.; Polizzi, J. M.; Cleiman, R. A.; Yi, J.; Romany, C. A. Tetrahedron Lett. 2002, 43, 7151.
40. Chen, M.-Y.; Patkar, L. N.; Jan, M.; Lee, A. S.; Lin, C. Tetrahedron Lett. 2004, 45, 635.
41. Gopinath, R.; Patel, B. K. Org. Lett. 2000, 2, 4177.
42. (a) Markiewicz, W. T. J. Chem. Res. (S) 1979, 24;
43. (b) Markiewicz, W. T.; Padyukova, N. S.; Samek, Z.; Smrt, J. Collect. Czech. Chem. Commun. 1980, 45, 1860.
44. (a) Karpeisky, A.; Gonzalez, C.; Burgin, A. B.; Beigelman, L. Tetrahedron Lett. 1998, 39, 1131;
45. (b) Nishizono, N.; Sumita, Y.; Ueno, Y.; Matsuda, A. Nucleic Acids Res. 1998, 26, 5067;
46. (c) Wang, G.; Girardet, J.-L.; Gunic, E. Tetrahedron, 1999, 55, 7707.
47. (a) Ziegler, T.; Eckhardt,; Neumann, K.; Birault, V. Synthesis, 1992, 1013;
48. (b) Ziegler, T.; Eckhardt, E. Tetrahedron Lett. 1992, 33, 6615;
49. (c) Krog-Jensen, C.; Oscarson, S. Carbohydr. Res. 1998, 308, 287.
50. (a) Rousse, B.; Puri, N.; Viswanadham, G.; Agback, C.; Glemarec, C.; Sandstrom, A.; Sund, C.; Chattopadhyaya, J. Tetrahedron, 1994, 50, 1777;
51. (b) Foldesi, A.; Nilson, F. P. R.; Glemarec, C.; Gioeli, C.; Chattopadhyaya, J. Tetrahedron, 1992, 48, 9033;
52. (c) Pfister, M.; Schirmeister, H.; Mohr, M.; Farkas, S.; Stengele, K.-P.; Reiner, T.; Dunkel, M.; Gokhale, S.; Charubala, R.; Pfleiderer, W. Helv. Chim. Acta, 1995, 78, 1705.