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Efficient Copper Bromide Catalyzed Chemoselective Thioacetalization of Carbonyl Compounds: Selectivity and Scope1

  • Varala, Ravi (Indian Institute of Chemical Technology) ;
  • Nuvula, Sreelatha (Indian Institute of Chemical Technology) ;
  • Adapa, Srinivas R. (Indian Institute of Chemical Technology)
  • Published : 2006.01.20

Abstract

Keywords

References

  1. IICT Communication no: 050614
  2. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; Wiley: New York, 1999; p 329
  3. Yus, M.; Najera, C.; Foubelo, F. Tetrahedron 2003, 59, 6147 https://doi.org/10.1016/S0040-4020(03)00955-4
  4. Corey, E. J.; Seebach, D. J. Org. Chem. 1966, 31, 4097 https://doi.org/10.1021/jo01350a052
  5. Seebach, D. Synthesis 1969, 17
  6. Grobel, B.-T.; Seebach, D. Synthesis 1977, 357
  7. Seebach, D. Angew. Chem. Int. Ed. Engl. 1979, 18, 239 https://doi.org/10.1002/anie.197902393
  8. Page, P. C. B.; van Niel, M. B.; Prodger, J. Tetrahedron 1989, 45, 7643 https://doi.org/10.1016/S0040-4020(01)85784-7
  9. Kocienski, P. J. Protecting Groups, 3rd ed.; Thieme: Stuttgart, 2004
  10. Ralls, J. W.; Dobson, R. M.; Reigel, B. J. Am. Chem. Soc. 1949, 71, 3320 https://doi.org/10.1021/ja01178a014
  11. Fieser, L. F. J. Am. Chem. Soc. 1954, 76, 1945 https://doi.org/10.1021/ja01636a063
  12. Djerassi, C.; Gorman, M. J. Am. Chem. Soc. 1953, 75, 3704 https://doi.org/10.1021/ja01111a029
  13. Mondal, E.; Sahu, P. R.; Bose, G.; Khan, A. T. Tetrahedron Lett. 2002, 43, 2843 https://doi.org/10.1016/S0040-4039(02)00345-3
  14. Ravindranathan, T.; Chavan, S. P.; Dantaled, S. W. Tetrahedron Lett. 1995, 36, 2285 https://doi.org/10.1016/0040-4039(95)00191-E
  15. Burczyk, B.; Kortylewicz, Z. Synthesis 1982, 831
  16. Firouzabadi, H.; Iranpoor, N.; Karimi, B. Synthesis 1999, 58
  17. Yadav, J. S.; Reddy, B. V. S.; Pandey, S. K. Synlett 2001, 238
  18. Ong, B. S. Tetrahedron Lett. 1980, 21, 4225 https://doi.org/10.1016/S0040-4039(00)92868-5
  19. Kumar, V.; Dev, S. Tetrahedron Lett. 1983, 24, 1289 https://doi.org/10.1016/S0040-4039(00)81637-8
  20. Karimi, B.; Seradj, H. Synlett 2000, 805
  21. Saraswathy, V. G.; Sankararaman, S. J. Org. Chem. 1994, 59, 4665 https://doi.org/10.1021/jo00095a049
  22. Muthusamy, S.; Babu, S. A.; Gunanathan, C. Tetrahedron Lett. 2001, 42, 359 https://doi.org/10.1016/S0040-4039(00)01966-3
  23. Kamal, A.; Chouhan, G. Tetrahedron Lett. 2002, 43, 1347 https://doi.org/10.1016/S0040-4039(01)02378-4
  24. Firouzabadi, H.; Iranpoor, N.; Hazarkhani, H. J. Org. Chem. 2001, 66, 7527 https://doi.org/10.1021/jo015798z
  25. De, S. K. Tetrahedron Lett. 2004, 45, 2339 https://doi.org/10.1016/j.tetlet.2004.01.106
  26. De, S. K. Adv. Synth. Catal. 2005, 347, 673 https://doi.org/10.1002/adsc.200404323
  27. De, S. K. Tetrahedron Lett. 2004, 45, 1035 https://doi.org/10.1016/j.tetlet.2003.11.082
  28. Muthusamy, S.; Babu, S. A.; Gunanathan, C. Tetrahedron 2002, 58, 7897 https://doi.org/10.1016/S0040-4020(02)00897-9
  29. Srivastava, N.; Dasgupta, S. K.; Banik, B. K. Tetrahedron Lett. 2003, 44, 1191 https://doi.org/10.1016/S0040-4039(02)02821-6
  30. Mandal, P. K.; Roy, S. C. Tetrahedron 1995, 51, 7823 https://doi.org/10.1016/0040-4020(95)00399-S
  31. Kamal, A.; Chouhan, G. Adv. Synth. Catal. 2004, 346, 579 https://doi.org/10.1002/adsc.200303171
  32. Ali, M. H.; Gomes, M. G. Synthesis 2005, 1326
  33. Varala, R.; Ramu, E.; Alam, M. M.; Adapa, S. R. Synlett 2004, 1747
  34. Varala, R.; Ramu, E.; Alam, M. M.; Adapa, S. R. Chem. Lett. 2004, 33, 1614 https://doi.org/10.1246/cl.2004.1614
  35. Varala, R.; Ramu, E.; Adapa, S. R. Bull. Chem. Soc. Jpn. 2006, 79, 140 https://doi.org/10.1246/bcsj.79.140
  36. Varala, R.; Alam, M. M.; Adapa, S. R. Synlett 2003, 720
  37. Alam, M. M.; Varala, R.; Adapa, S. R. Tetrahedron Lett. 2003, 5115
  38. Varala, R.; Alam, M. M.; Adapa, S. R. Synlett 2003, 67
  39. Varala, R.; Ramu, E.; Sreelatha, N.; Adapa, S. R. Tetrahedron Lett. 2006, 47, 877 https://doi.org/10.1016/j.tetlet.2005.12.005
  40. Alam, M. M.; Varala, R.; Ramu, E.; Adapa, S. R. Lett. Org. Chem. 2006, 3, 187 https://doi.org/10.2174/157017806775789930
  41. Xu, L.-W.; Li, J.-W.; Xia, C.-G.; Zhou, S.-L.; Hu, X.-X. Synlett 2003, 2425
  42. Park, S. B.; Alper, H. Chem. Commun. 2005, 1315
  43. Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 11810 https://doi.org/10.1021/ja0460763
  44. Li, C.-J. Wei, C. Chem. Commun. 2002, 268
  45. Gommermann, N.; Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem. Int. Ed. 2003, 42, 5763 https://doi.org/10.1002/anie.200352578
  46. Koradin, C.; Gommermann, N.; Polborn, K.; Knochel, P. Chem. Eur. J. 2003, 9, 2797 https://doi.org/10.1002/chem.200204691
  47. Li, Z.; Li, C.-J. Eur. J. Org. Chem. 2005, 15, 3173

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