Development of a mild procedure for the addition of bisulfite to electrophilic olefins

Advanced Synthesis and Catalysis

Volumn 352, Issue 18, 2010, Pages 3163-3168

  Fini, Francesco ^a   Nagabelli, Murali ^a   Adamo, Mauro F A ^a  

^a ROYAL COLLEGE OF SURGEONS IN IRELAND   (Ireland)

Author keywords

alkenes; amine catalysis; sulfonic acids; thia Mchael addition; triethylamine

Indexed keywords

EID: 78650411184     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000543     Document Type: Article

References (41)

1. F. G. Bordwell, D. Algrim, J. Org. Chem. 1976, 41, 2507.
2. R. Yoshioka, K. Okamura, S. Yamada, K. Aoe, T. Da-Te, Bull. Chem. Soc. Jpn. 1998, 71, 1109
3. H. Kawanishi, H. Morimoto, T. Nakano, T. Watanabe, K. Oda, K. Tsujihara, Heterocycles 1998, 49, 181.
4. T. R. Vries, H. Wynberg, E. van Echten, J. Koek, W. ten Hoeve, R. M. Kellogg, Q. B. Broxterman, A. Minnaard, B. Kaptein, S. van der Sluis, L. A. Hulshof and J. Kooistra, Angew. Chem. 1998, 110, 2491
5. Angew. Chem. Int. Ed. Engl. 1998, 37, 2349.
6. R. M. Kellogg, J. W. Nieuwenhuijzen, K. Pouwer, T. R. Vries, Q. B. Broxterman, R. F. P. Grimbergen, B. Kaptein, R. M. La Crois, E. de Wever, K. Zwaagstra and A. C. van der Laan, Synthesis 2003, 1626.
7. The Chemistry of Sulfonic Acids, Esters and their Derivatives, (Eds.:, S. Patai, Z. Rappoport,), John Wiley & Sons, New York, 1991.
8. P. Krogsgaard-Larsen, in: Comprehensive Medicinal Chemistry, Vol. 3, (Eds.:, P. G. Sammes, J. B. Taylor,), Pergamon, Oxford, 1990, p 433
9. D. R. Curtis, J. C. Watkins, Pharmacol. Rev. 1965, 17, 347
10. D. R. Curtis, J. C. Watkins, Nature 1961, 191, 1010
11. J. M. Crawford, Biochem. Pharmacol. 1963, 12, 1443
12. J. M. Crawford, D. R. Curtis, Br. J. Pharmacol. 1964, 23, 313.
13. M. Yoshikawa, S. Yamaguchi, K. Kunimi, H. Matsuda, J. Yamahara, N. Murakami, Chem. Pharm. Bull. 1994, 42, 1226.
14. E. J. Corey, K. Cimprich, Tetrahedron Lett. 1992, 33, 4099.
15. D. Braghiroli, E. Mussati, M. Di Bella, M. Saladini, Tetrahedron: Asymmetry 1996, 7, 831
16. D. Braghiroli, M. Di Bella, Tetrahedron: Asymmetry 1997, 8, 2209
17. D. Braghiroli, M. Di Bella, Tetrahedron Lett. 1996, 37, 7319.
18. D. Enders, N. Vignola, O. M. Berner, J. W. Bats, Angew. Chem. 2002, 114, 116
19. Angew. Chem. Int. Ed. 2002, 41, 109
20. D. Enders, O. M. Berner, N. Vignola, J. W. Bats, Chem. Commun. 2001, 2489
21. D. Enders, O. M. Berner, N. Vignola, W. Harnying, Synthesis 2002, 1945.
22. D. Enders, S. Wallert, Synlett 2002, 304
23. D. Enders, S. Wallert, J. Rusnik, Synthesis 2003, 1856.
24. D. Enders, K. Hoffman, Eur. J. Org. Chem. 2009, 1665.
25. F. K. Beilstein, H. Wiegand, Ber. Dtsch. Chem. Ges. 1885, 18, 482
26. R. T. E. Schenk, I. Danishefsky, J. Org. Chem. 1951, 16, 1683
27. M. F. Browne, R. L. Shiner, J. Org. Chem. 1957, 22, 1320
28. I. H. Pitman, E. Shefter, M. Ziser, J. Am. Chem. Soc. 1970, 92, 3413.
29. M. L. Crawley, E. McLaughlin, W. Zhu, A. Combs, Org. Lett. 2005, 7, 5067.
30. R. Maylor, J. B. Gill, D. C. Goodall, J. Chem. Soc. Dalton Trans. 1972, 2001.
31. B. Springs, P. Haake, J. Org. Chem. 1977, 42, 472.
32. See Supporting Information.
33. M. V. Gorelik, S. V. Bogdanov, A. N. Rodionov, Zh. Obshch. Khim. 1960, 30, 2959.
34. Large excesses of triethylamine and bisulfite were needed to bring reactions to completion.
35. A. Baschieri, L Bernardi, A. Ricci, S. Suresh, M. F. A. Adamo, Angew. Chem. 2009, 121, 9506
36. Angew. Chem. Int. Ed. 2009, 48, 9342.
37. In other studies, styryl nitroisoxazoles 2 showed faster reactivity compared to chalcones; in this context the slower reactivity observed is attributed to the poor solubility of these starting materials in the hydroalcoholic medium.
38. M. F. A. Adamo, European Patent Application 08021530.4
39. M. F. A. Adamo, United Kingdom Patent Application 0910726.9
40. M. F. A. Adamo, International Application PCT/EP2009/008890.
41. A 5-mL syringe packed with acidic ion exchange resin (3 mL, ca. 2.2 g) was washed with 6 M HCl (4× 3 mL) and then with deionized water (4× 3 mL). After that the resin pad was ready to be used.