Catalyst-free conjugated addition of thiols to α,β-unsaturated carbonyl compounds in water

Organic Letters

Volumn 8, Issue 11, 2006, Pages 2433-2436

  Khatik, Gopal L ^a   Kumar, Raj ^a   Chakraborti, Asit K ^a  

^a NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

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Indexed keywords

EID: 33745697764     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060846t     Document Type: Article

References (41)

1. Bakuzia, P.; Bakuzis, M. L. F. J. Org. Chem. 1981, 46, 235.
2. Cherkauskas, J. P.; Cohen, T. J. Org. Chem. 1992, 57, 6.
3. Trost, B. M.; Keeley, D. E. J. Org. Chem. 1975, 40, 2013.
4. Cohen, T.; Mura, A. J., Jr.; Shull, D. W.; Fogel, E. R.; Ruffner, R. J.; Falck, J. R. J. Org. Chem. 1976, 41, 3218.
5. Fujita, E.; Nagao, Y. Bioorg. Chem. 1977, 6, 287.
6. (a) Fluharty, A. L. In The Chemistry of the Thiol Group; Patai, S., Ed.; Wiley Interscience: New York, 1974; p 589, Part 2.
7. (b) Kumar, A.; Salunkhe, R. V.; Rane, R. A.; Dike, S. Y. J. Chem. Soc., Chem. Commun. 1991, 485.
8. (a) Zeolites: Sreekumar, R.; Rugmini, P.; Padmakumar, R. Tetrahedron Lett. 1997, 38, 6557.
9. 2: Saito, M.; Nakajima, M.; Hashimoto, S. Tetrahedron 2000, 56, 9589.
10. 3: Kobyashi, S.; Ogawa, C.; Kawamura, M.; Sugiura, M. Synlett. 2001, 983.
11. 3: Bandini, M.; Cozzi, P. G.; Giacomini, M.; Melchiorre, P.; Selva, S.; Umani-Ronchi, A. J. Org. Chem. 2002, 67, 3700.
12. 7: Zahouily, M.; Abrouki, Y.; Rayadh, A. Tetrahedron Lett. 2002, 43, 7729.
13. (f) KF/NP: Abrouki, Y.; Zahouily, M.; Rayadh, A.; Bahlaouan, B.; Sebti, S. Tetrahedron Lett. 2002, 43, 8951.
14. 3: Cheng, S.; Comer, D. D. Tetrahedron Lett. 2002, 43, 1179.
15. 3: Alam, M. M.; Varala, R.; Adapa, S. R. Tetrahedron Lett. 2003, 44, 5115.
16. 3: Srivastava, N.; Banik, B. K. J. Org. Chem. 2003, 68, 2109.
17. (j) Nafion SAC-13: Wabnitz, T. C.; Yu, J.-Q.; Spencer, J. B. Synlett 2003, 1070.
18. (k) Ionic liquids: Yadav, J. S.; Reddy, B. V. S.; Baishya, G. J. Org. Chem. 2003, 68, 7098.
19. Ranu, B. C.; Dey, S. S.; Hajra, A. Tetrahedron 2003, 59, 2417.
20. Ranu, B. C.; Dey, S. S. Tetrahedron 2004, 60, 4183.
21. 3: Ranu, B. C.; Dey, S. S.; Samanta, S. ARKIVOC 2005 (iii), 44.
22. 2: Garg, S. K.; Kumar, R.; Chakraborti, A. K. Tetrahedron Lett. 2005, 46, 1721.
23. 2: Garg, S. K.; Kumar, R.; Chakraborti, A. K. Synlett 2005, 1370.
24. 2: Chu, C-M.; Gao, S.; Sastry, M. N. V.; Yao, C.-F. Tetrahedron Lett. 2005, 46, 4971.
25. (a) Naidu, B. N.; Sorenson, M. E.; Connolly, T. P.; Ueda, Y. J. Org. Chem. 2003, 68, 10098.
26. (b) Firouzabadi, H.; Iranpoor, N.; Jafari, A. A. Adv. Synth. Catal. 2005, 347, 655.
27. (c) Krishnaveni, N. S.; Surendra, K.; Rao, K. R. Chem. Commun. 2005, 669.
28. Tundo, P.; Anastas, P.; Black, D. S.; Breen, J.; Collins, T.; Memoli, S.; Miyamoto, J.; Polyakoff, M.; Tumas, W. Pure Appl. Chem. 2000, 72, 1207.
29. (a) Organic Synthesis in Water: Grieco, P. A., Ed.; Blackie Academic and Professional: London, 1998.
30. Li, C. J.; Chang, T. H. Organic Reactions in Aqueous Media; Wiley: New York, 1997.
31. (b) Azizi, N.; Saidi, M. R. Org. Lett. 2005, 7, 3649.
32. Other examples of Michael reactions in water: (a) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496.
33. (b) Larpent, C.; Patin, H. Tetrahedron 1988, 44, 6107.
34. (c) Larpent, C.; Meignan, G.; Patin, H. Tetrahedron 1990, 46, 6381.
35. (d) Jenner, G. Tetrahedron 1996, 52, 13557.
36. (e) Keller, R.; Feringa, B. L. Tetrahedron Lett. 1996, 37, 1879.
37. (f) Mori, Y.; Kakumoto, K.; Manabe, K.; Kobayashi, S. Tetrahedron Lett. 2000, 41, 3107.
38. Elkington, J. http://www.sustainability.co.uk/sustainability.htm>.
39. Besra, R. C.; Rudrawar, S.; Chakraborti, A. K. Tetrahedron Lett. 2005, 46, 6213.
40. (a) Chakraborti, A. K.; Sharma, L.; Nayak, M. K. J. Org. Chem. 2002, 67, 2541.
41. (b) Nayak, M. K.; Chakraborti, A. K. Chem. Lett. 1998, 297.