Efficient copper bromide catalyzed chemoselective thioacetalization of carbonyl compounds: Selectivity and scope

Bulletin of the Korean Chemical Society

Volumn 27, Issue 7, 2006, Pages 1079-1082

  Varala, Ravi ^a   Nuvula, Sreelatha ^a   Adapa, Srinivas R ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Carbonyl compounds; Chemoselectivity; Copper bromide (Cu(I)Br); Thioacetalization

Indexed keywords

EID: 33746364802     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2006.27.7.1079     Document Type: Article

References (47)

1. IICT Communication no: 050614.
2. rd ed.; Wiley: New York, 1999; p 329.
3. (b) Yus, M.; Najera, C.; Foubelo, F. Tetrahedron 2003, 59, 6147.
4. (a) Corey, E. J.; Seebach, D. J. Org. Chem. 1966, 31, 4097.
5. (b) Seebach, D. Synthesis 1969, 17.
6. (c) Grobel, B.-T.; Seebach, D. Synthesis 1977, 357.
7. (d) Seebach, D. Angew. Chem. Int. Ed. Engl. 1979, 18, 239.
8. (e) Page, P. C. B.; van Niel, M. B.; Prodger, J. Tetrahedron 1989, 45, 7643.
9. (f) Kocienski, P. J. Protecting Groups, 3rd ed.; Thieme: Stuttgart, 2004.
10. There have been a number of reports on the protection of carbonyl compounds as dithioacetals. (a) HCl: Ralls, J. W.; Dobson, R. M.; Reigel, B. J. Am. Chem. Soc. 1949, 71, 3320.
11. 2O: Fieser, L. F. J. Am. Chem. Soc. 1954, 76, 1945.
12. (c) PTSA: Djerassi, C.; Gorman, M. J. Am. Chem. Soc. 1953, 75, 3704.
13. 3: Mondal, E.; Sahu, P. R.; Bose, G.; Khan, A. T. Tetrahedron Lett. 2002, 43, 2843.
14. (e) TMSOTf: Ravindranathan, T.; Chavan, S. P.; Dantaled, S. W. Tetrahedron Lett. 1995, 36, 2285.
15. 2: Burczyk, B.; Kortylewicz, Z. Synthesis 1982, 831.
16. (g) LiBr: Firouzabadi, H.; Iranpoor, N.; Karimi, B. Synthesis 1999, 58.
17. 4: Yadav, J. S.; Reddy, B. V. S.; Pandey, S. K. Synlett 2001, 238.
18. 3: Ong, B. S. Tetrahedron Lett. 1980, 21, 4225.
19. 4: Kumar, V.; Dev, S. Tetrahedron Lett. 1983, 24, 1289.
20. 4: Karimi, B.; Seradj, H. Synlett 2000, 805.
21. 4: Saraswathy, V. G.; Sankararaman, S. J. Org. Chem. 1994, 59, 4665.
22. 3: Muthusamy, S.; Babu, S. A.; Gunanathan, C. Tetrahedron Lett. 2001, 42, 359.
23. 3: Kamal, A.; Chouhan, G. Tetrahedron Lett. 2002, 43, 1347.
24. 2: Firouzabadi, H.; Iranpoor, N.; Hazarkhani, H. J. Org. Chem. 2001, 66, 7527.
25. 3: De, S. K. Tetrahedron Lett. 2004, 45, 2339.
26. (q) De, S. K. Adv. Synth. Catal. 2005, 347, 673.
27. 2: De, S. K. Tetrahedron Lett. 2004, 45, 1035.
28. 3: Muthusamy, S.; Babu, S. A.; Gunanathan, C. Tetrahedron 2002, 58, 7897.
29. 3: Srivastava, N.; Dasgupta, S. K.; Banik, B. K. Tetrahedron Lett. 2003, 44, 1191.
30. (u) CAN: Mandal, P. K.; Roy, S. C. Tetrahedron 1995, 51, 7823.
31. (v) Ionic liquid [bmim]Br: Kamal, A.; Chouhan, G. Adv. Synth. Catal. 2004, 346, 579.
32. (w) p-TsOH/silica gel: Ali, M. H.; Gomes, M. G. Synthesis 2005, 1326.
33. (a) Varala, R.; Ramu, E.; Alam, M. M.; Adapa, S. R. Synlett 2004, 1747.
34. (b) Varala, R.; Ramu, E.; Alam, M. M.; Adapa, S. R. Chem. Lett. 2004, 33, 1614.
35. (c) Varala, R.; Ramu, E.; Adapa, S. R. Bull. Chem. Soc. Jpn. 2006, 79, 140.
36. (d) Varala, R.; Alam, M. M.; Adapa, S. R. Synlett 2003, 720.
37. (e) Alam, M. M.; Varala, R.; Adapa, S. R. Tetrahedron Lett. 2003, 5115.
38. (f) Varala, R.; Alam, M. M.; Adapa, S. R. Synlett 2003, 67.
39. (g) Varala, R.; Ramu, E.; Sreelatha, N.; Adapa, S. R. Tetrahedron Lett. 2006, 47, 877.
40. (h) Alam, M. M.; Varala, R.; Ramu, E.; Adapa, S. R. Lett. Org. Chem. 2006, 3, 187.
41. (a) Xu, L.-W.; Li, J.-W.; Xia, C.-G.; Zhou, S.-L.; Hu, X.-X. Synlett 2003, 2425.
42. (b) Park, S. B.; Alper, H. Chem. Commun. 2005, 1315.
43. (c) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 11810.
44. (d) Li, C.-J. Wei, C. Chem. Commun. 2002, 268.
45. (e) Gommermann, N.; Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem. Int. Ed. 2003, 42, 5763.
46. (f) Koradin, C.; Gommermann, N.; Polborn, K.; Knochel, P. Chem. Eur. J. 2003, 9, 2797.
47. (g) Li, Z.; Li, C.-J. Eur. J. Org. Chem. 2005, 15, 3173.