Thia-Michael addition reactions in water using 3-[bis(Alkylthio) methylene]pentane-2,4-diones as odorless and efficient thiol equivalents

Letters in Organic Chemistry

Volumn 4, Issue 4, 2007, Pages 281-284

  Chai, Yanyan ^a   Dong, Dewen ^a,b   Ouyang, Yan ^a   Liang, Yongjiu ^a   Wang, Yan ^a   Li, Minghui ^a   Liu, Qun ^a  

^a NORTHEAST NORMAL UNIVERSITY   (China)

^b CHANGCHUN INSTITUTE OF APPLIED CHEMISTRY   (China)

Author keywords

keto sulfides; unsaturated carbonyl compounds; ; Michael addition; P dodecylbenzenesulfonic acid; Water

Indexed keywords

EID: 35648997950     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017807781024318     Document Type: Article

References (53)

1. (a) Schmalz, H.-G. Comprehensive Organic Synthesis; Pergamon: Oxford, 1991; Vol. 4, Chapter 1.5, pp. 199;
2. (b) Perlmutter, P. Conjugated Addition Reactions in Organic Synthesis; Pergamon: Oxford, 1992; pp. 114;
3. (c) Sheldon, R. A. Chirotechnologies, Industrial Synthesis of Optically Active Compounds; Dekker Publishing: New York, 1993.
4. (a) Koyabashi, N.; Iwai, K. J. Am. Chem. Soc., 1978, 100, 7071;
5. (b) Hiemstra, H.; Wynberg, H J. Am. Chem. Soc., 1981, 103, 417.
6. (c) Gorthey, L. N.; Vairamani, M.; Djerassi, C. J. Org. Chem., 1985, 50, 4173;
7. (d) Bashiardes, G.; Davies, S. G. Tetrahedron Lett., 1987, 28, 5563;
8. (e) Sera, A.; Takagi, K.; Katayama, H.; Yamada, H.; Matsumoto, K. J. Org. Chem., 1988, 53, 1157;
9. (f) Cherkauskas, J. P.; Cohen, T. J. Org. Chem., 1992, 57, 6;
10. (g) Wu, M.-J.; Wu, C.-C.; Tseng, T.-C.; Pridgen, L.-N. J. Org. Chem., 1994, 59, 7188;
11. (h) Tomioka, K.; Muraoka, A.; Kanai, M. J. Org. Chem., 1995, 60, 6188;
12. (i) Nishimura, K.; Ono, M.; Nagaoka, Y.; Tomioka, K. J. Am. Chem. Soc., 1997, 119, 12974;
13. (j) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc., 1998, 120, 4043;
14. (k) Kanemasa, S.; Oderaotoshi, Y.; Wada, E. J. Am. Chem. Soc., 1999, 121, 8675;
15. (l) Koulocheri, S. D.; Magiatis, P.; Skaltsounis, A.; Haroutounian, S. A. Tetrahedron, 2000, 56, 6135;
16. (m) Nishimura, K.; Ono, M.; Nagaoka, Y.; Tomioka, K. Angew. Chem. Int. Ed., 2001, 40, 440;
17. (n) Athawale, V.; Manjrekar, N. Tetrahedron Lett., 2001, 42, 4541;
18. (o) Wabnitz, T.C.; Spencer, J. B. Org. Lett., 2003, 5, 2141;
19. (p) Matsumoto, K.; Watanabe, A.; Uchida, T.; Ogi, K.; Katsuki, T. Tetrahedron Lett., 2004, 45, 2385;
20. (q) Garg, S. K.; Kumar, R.; Chakraborti, A. K. Tetrahedron Lett., 2005, 46, 1721;
21. (r) Menand, M.; Dalla, V. Synlett, 2005, 95.
22. (a) Saito, M.; Nakajima, M.; Hashimoto, S. Tetrahedron, 2000, 41, 9589;
23. (b) Bandini, M.; Cozzi, P. G.; Giacomini, M.; Melchiorre, P.; Selva, S.; Umani-Ronchi, A. J. Org. Chem., 2002, 67, 3700;
24. (c) Garg, S. K.; Kumar, R.; Chakraborti, A. K. Synlett, 2005, 1370.
25. (a) Srivastava, N.; Banik. B. K. J. Org. Chem., 2003, 68, 2109.
26. (a) Zahouily, M.; Abrouki, Y.; Rayadh, A. Tetrahedron Lett., 2002, 43 7729;
27. (b) Abrouki, Y.; Zahouily, M.; Rayadh, A.; Bahlaouan, B.; Sebti, S. Tetrahedron Lett., 2002, 43, 8951.
28. (a) Kobayashi, S.; Ogawa, C.; Kawamura, M.; Sugiura, M. Synlett, 2001, 983;
29. (b) Alam, M. M.; Varala, R.; Adapa, S. R. Tetrahedron Lett., 2003, 44, 5115.
30. (a) Sreekumar, R.; Rugmini, P.; Padmakumar, R. Tetrahedron Lett., 1997, 38, 6557.
31. (b) Wabnitz, T.C.; Yu, J.-Q.; Spencer, J. B. Synlett, 2003, 1070;
32. (c) Cheng, S.; Comer, D. D. Tetrahedron Lett., 2002, 43, 1179.
33. (d) Firouzabadi, H.; Iranpoor, N.; Jafari, A. A. Synlett 2005, 299.
34. (a) Ranu, B. C.; Dey, S. S. Hajra, A. Tetrahedron, 2003, 59, 2417;
35. (b) Ranu, B. C.; Dey, S. S. Tetrahedron Lett., 2004, 60, 4183.
36. (a) Node, M.; Kumar, K.; Nishide, K.; Ohsugi, S.; Miyamoto, T. Tetrahedron Lett., 2001, 42, 9207;
37. (b) Nishide, K.; Miyamoto, T.; Kumar, K.; Ohsugi, S. I.; Node, M. Tetrahedron Lett., 2002, 43, 8569;
38. (c) Nishide, K.; Ohsugi, S.; Fudesaka, M.; Kodama, S.; Node, M. Tetrahedron Lett., 2002, 43, 5177.
39. Nishide, K.; Ohsugi, S.; Shiraki, H.; Tamakita, H.; Node, M. Org. Lett., 2001, 3, 3121.
40. (a) Bertini, V.; Lucchesini, F.; Pocci, M.; De Munno, A. Tetrahedron Lett., 1998, 39, 9263;
41. (b) Bertini, V.; Lucchesini, F.; Pocci, M.; De Munno, A. J. Org. Chem., 2000, 65, 4839;
42. (c) Bertini, V.; Pocci, M.; Lucchesini, F.; Alfei, S.; De Munno, A. Synlett, 2003, 864.
43. (a) Iimura, S.; Manabe, K.; Kobayashi, S. Org. Lett., 2003, 5, 101;
44. (b) Miyazaki, T.; Han-ya, Y.; Tokuyama, H.; Fukuyama, T. Synlett, 2004, 477.
45. Ranu, B. C.; Mandal, T. Synlett, 2004, 1239.
46. (a) Liu, Q.; Che, G.; Yu, H.; Liu, Y.; Zhang, J.; Zhang, Q.; Dong, D. J. Org. Chem., 2003, 68, 9148;
47. (b) Yu, H.; Liu, Q.; Yin, Y.; Fang, Q.; Zhang, J.; Dong, D. Synlett, 2004, 999;
48. (c) Dong, D.; Ouyang, Y.; Yu, H.; Liu, Q.; Liu, J.; Wang, M.; Zhu, J. J. Org. Chem., 2005, 70, 4535;
49. (d) Liu, J.; Liu, Q.; Yu, H.; Ouyang, Y.; Dong, D. Synth. Commun., 2004, 34, 4545;
50. (e) Yu, H.; Dong, D.; Ouyang, Y.; Liu, Q. Can. J. Chem., 2005, 83, 1741.
51. (a) Yu, H.; Dong, D.; Ouyang, Y.; Liu, Q.; Wang, Y. Lett. Org. Chem., 2005, 2, 755;
52. (b) Dong, D.; Yu, H.; Ouyang, Y.; Liu, Q.; Bi, X.; Lu, Y. Synlett, 2006, 283.
53. Ouyang, Y.; Dong, D.; Yu, H.; Liang, Y.; Liu, Q. Adv. Synth. Catal., 2006, 348, 206.