O-benzenedisulfonimide as a reusable brnsted acid catalyst for hetero-michael reactions

Synthetic Communications

Volumn 43, Issue 5, 2013, Pages 758-767

  Barbero, Margherita ^a   Cadamuro, Silvano ^a   Dughera, Stefano ^a  

^a UNIVERSITY OF TURIN   (Italy)

Author keywords

Brnsted acid; conjugate addition; homogeneous catalysis; Michael reaction; recyclable catalyst

Indexed keywords

BENZENE DERIVATIVE; BRONSTED ACID; NITROGEN; NUCLEOPHILE; OXYGEN; SULFUR;

ARTICLE; CATALYSIS; CATALYST; MICHAEL ADDITION;

EID: 84869464357     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2011.614834     Document Type: Article

References (34)

1. (a) Jung, M. E. Additions to and substitutions at C-C p-bonds; In Comprehensive Organic Synthesis; B. M. Trost, I. Fleming (Eds.); Pergamon: Oxford, 1990; vol. 4, pp. 1-67;
2. (b) Pelmutter, P. Conjugate addition reaction in organic synthesis; In Tetrahedron Organic Chemistry Series; Pergamon: Oxford, 1992; vol. 9.
3. (a) Misra, M.; Luthra, R.; Singh, K. L.; Sushil, K. Amino acids, peptides, porphyrins, and alkaloids; In Comprehensive Natural Products Chemistry; D. H. R. Barton, K. Nakanishi and O. Meth-Cohnd (Eds); Pergamon: Oxford, 1999; vol. 4;
4. (b) Banik, B. K.; Becker, F. F.; Banik, I. Bioorg. Med. Chem. 2004, 12, 2523-2528;
5. (c) Nising, C. F.; Braese, S. Chem. Soc. Rev. 2008, 37, 1218-1228.
6. (a) Cardillo, C.; Tomasini, C. Chem. Soc. Rev. 1996, 25, 117-128;
7. (b) Juaristi, E.; Lopez-Ruiz, H. Curr. Med. Chem. 1999, 983-1004.
8. (a) Fujita, E.; Nagao, Y. Bioorg. Chem. 1977, 6, 287-309;
9. (b) Alam, M. M.; Varala, R.; Adapa, S. R. Tetrahedron Lett. 2003, 44, 5115-5119;
10. (c) Movassagh, B.; Shaygana, P. Arkivoc 2006, 12, 130-137.
11. (a) Trost, B. M.; Keeley, D. E. J. Org. Chem. 1975, 40, 2013;
12. (b) Bakuzis, P.; Bakuzis, M. L. F. J. Org. Chem. 1981, 46, 235-237;
13. (c) Cherkauskas, J. P.; Cohen, T. J. Org. Chem. 1992, 57, 6-8;
14. (d) Kumar, A.; Salunkhe, R. V.; Rane, R. A.; Dike, S. Y. J. Chem. Soc., Chem. Commun. 1991, 485-486.
15. Yadav, J. S.; Ramesh Reddy, A.; Gopal Rao, Y.; Narsaiah, A. V.; Subba Reddy, B. V. Synthesis 2007, 3447-3450, and references therein.
16. (a) Sharma, Y. O.; Degani, M. S. J. Mol. Catal. A: Chem. 2007, 277, 215-220;
17. (b) Yu, C.-J.; Liu, C.-J. Gaodeng Xuexiao Huaxue Xuebao 2010, 31, 1158-1161; Chem. Abstr. 2010, 153, 406208;
18. (c) Karodia, N.; Liu, X.; Ludley, P.; Pletsas, D.; Stevenson, G. Tetrahedron 2006, 62, 11039-11043;
19. (d) Guo, H.; Li, X.; Wang, J.-L.; Jin, X.-H.; Lin, X.-F. L. Tetrahedron 2010, 66, 8300-8303.
20. (a) De, K.; Legros, J.; Crousse, B.; Bonnet-Delpon, D. J. Org. Chem. 2009, 74, 6260-6265;
21. (b) Ranu, B. C., Banerjee, S. Tetrahedron Lett. 2007, 48, 141-143;
22. (c) Zou, B.; Jiang, H.-F. Chin. J. Chem. 2008, 26, 1309-1314.
23. (a) Wabnitz, T. C.; Spencer, J. B. Org. Lett. 2003, 5, 2141-2144;
24. (b) Hong, Y.-M.; Shen, Z.-L.; Hu, X.-Q.; Mo, W.-M.; He, X.-F.; Hu, B.-X.; Sun, N. Arkivoc 2009, 14, 146-155;
25. (c) Singh, R., Goswani, T. J. Phys. Org. Chem. 2008, 21, 225-236.
26. (a) Wang, Y.; Yuan, Y.-Q.; Guo, S.-R. Molecules 2009, 14, 4779-4789;
27. (b) Sharma, G.; Kumar, R.; Chakraborti, A. K. Tetrahedron Lett. 2008, 49, 4272-4275;
28. (c) Shaikh, N. S.; Deshpande, V. H.; Bedekar, A. V. Tetrahedron 2001, 57, 9045-9048;
29. (d) Wabnitz, T. C.; Yu, J.-Q.; Spencer, J. B. Synlett 2003, 1070-1072;
30. (e) Polshettiwar, V.; Varma, R. S. Tetrahedron Lett. 2007, 48, 8735-8738;
31. (f) Singh, S. P.; Kumar, T. V.; Chandrasekharam, M.; Giribabu, L.; Yella Reddy, P. Synth. Commun. 2009, 39, 3982-3989.
32. (a) Barbero, M.; Bazzi, S.; Cadamuro, S.; Dughera, S. Curr. Org. Chem. 2011, 15, 576-599, and references therein;
33. (b) Barbero, M.; Cadamuro, S.; Dughera, S.; Venturello, P. Synlett 2007, 2209-2212;
34. (c) Barbero, M.; Cadamuro, S.; Dughera, S.; Ghigo, G. Org. Biomol. Chem. 2012, 10, 4058-4068.