Stereoselective one-pot synthesis of highly differently substituted thiochromans

Tetrahedron Letters

Volumn 50, Issue 47, 2009, Pages 6466-6468

  Seifert, Andrea ^a   Mahrwald, Rainer ^a  

^a HUMBOLDT UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

THIOCHROMAN DERIVATIVE; TRIFLUOROACETIC ACID;

ALDOL REACTION; ARTICLE; CATALYSIS; CROSS COUPLING REACTION; CYCLIZATION; ONE POT SYNTHESIS; REACTION OPTIMIZATION; ROOM TEMPERATURE; STEREOCHEMISTRY;

EID: 77951168194     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.09.009     Document Type: Article

References (37)

1. Schneller, A. S. In Advances in Heterocyclic Chemistry; Katrizky, A. R., Boulton, A. J., Eds.; Academic Press: New York, 1975; Vol. 18, pp 59-97.
2. Chu, D. T. W.; James, D. R., Wang, B. PCT Int. Appl. 2006, WO 2006093548; CAN: 145:28511195.
3. Thorberg, S.-O. PCT Int. Appl. 2004, WO 2004110430; CAN: 142:32982.
4. Thorberg, S.-O. PCT Int. Appl. 2004, WO 2004110429; CAN: 142:32981.
5. Warawa, E. J.; McLaren, C. D.; Simon-Bierenbaum, R. E. PCT Int. Appl. 2000, WO 2000078751.
6. Okamachi, A.; Hatanaka, T.; Sugano, K.; Hayashi, Y. PCT Int. Appl. 1999, WO 9964408.;
7. (b) Yoshitake, K.; Myung-Hwa, K.; Masahiro, N.; Yoshihito, O.; Toshiaki, T.; Kenji, T.; Iwao, O.; Shin-ichi, K.; Yoshiaki, N.; Setsu, K.; Kazumi, M.; Jae-Chon, J.; Hee-An, K.; Hyun-Suk, L.; Hak-Yeop, K. Biorg. Med. Chem. Lett. 2006, 16, 4090-4094.
8. Bolognesi, M. L.; Bartolini, M.; Cavalli, A.; Andrisano, V.; Rosini, M.; Minarini, A.; Melchiorre, C. J. Med. Chem. 2004, 47, 5945-5952.
9. van Vliet, L. A.; Rodenhuis, N.; Dijkstra, D.; Wikström, H.; Pugsley, T. A.; Serpa, K. A.; Meltzer, L. T.; Heffner, T. G.; Wise, L. D.; Lajiness, M. E.; Huff, R. M.; Svensson, K.; Lundmark, M.; Sundell, S. J. Med. Chem. 2000, 43, 2871-2882.
10. Xia, P.; Yin, Z. J.; Chen, Y.; Zhang, Q.; Zhang, B.; Xia, Y.; Yang, Z. Y.; Kilgore, N.; Wild, C.; Morris-Natschke, S. L.; Lee, K. H. Biorg. Med. Chem. Lett. 2004, 14, 3341-3343.
11. (a) Meyers, C. Y.; Rinaldi, C.; Bonoli, L. J. Org. Chem. 1963, 28, 2440-2442;
12. (b) Bopalan, B.; Rajagopalan, K.; Swaminathan, S. Synthesis 1976, 409-411;
13. (c) Katritzky, A. R.; Akhmedov, N. G.; Wang, M.; Rostek, C. J.; Steel, P. J. Magn. Res. Chem. 2004, 42, 999-1011;
14. (d) Das, B.; Chowdhury, N.; Damodar, K.; Banerjee, J. Chem. Pharm. Bull. 2007, 55, 1274-1276.
15. (a) Waugh, K. M.; Berlin, K. D.; Ford, W. T.; Holt, E. M.; Carrol, J. P.; Schomber, P. R.; Thompson, M. D.; Schiff, L. J. J. Med. Chem. 1985, 28, 116-124;
16. (b) Jensen, A. W.; Menczuk, J.; Nelson, D.; Caswell, O.; Fleming, S. A. J. Heterocycl. Chem. 2000, 37, 1527-1531; For more intensively theoretical investigations of this reaction see:
17. (c) Skarzewski, J.; Zielinska-Blajet, M.; Roszak, S.; Turowska-Tyrk, I. Tetrahedron 2003, 59, 3621-3626.
18. (a) Cossy, J.; Leblanc, H. C. Tetrahedron Lett. 1987, 28, 1417-1418;
19. (b) Labiad, B.; Villemin, D. Synth. Commun. 1989, 19, 31-38;
20. (c) Ishino, Y.; Nakamura, M.; Nishiguchi, I.; Hirashima, T. Synlett 1991, 633-635;
21. (d) Ishino, Y.; Mihara, M.; Kawai, H. Synlett 2001, 8, 1317-1319;
22. (e) Jafarzadeh, M.; Amani, K.; Nikpour, F. Tetrahedron Lett. 2005, 46, 7567-7569;
23. (f) Aoyama, T.; Okada, K.; Nakajima, H.; Matsumoto, T.; Takido, T.; Kodomari, M. Synlett 2007, 387-390;
24. (g) Sowmiya, M.; Sharma, A.; Parsodkar, S.; Mishra, B. G.; Dubey, A. Appl. Catal., A 2007, 333, 272-280.
25. (a) Rios, R.; Sunden, H.; Ibrahem, I.; Zhao, G.-L.; Eriksson, L.; Cordova, A. Tetrahedron Lett. 2006, 47, 8547-8551;
26. (b) Wang, W.; Li, H.; Wang, J.; Zu, L. J. Am. Chem. Soc. 2006, 128, 10354-10355.
27. Rios, R.; Sunden, H.; Ibrahem, I.; Zhao, G.-L.; Cordova, A. Tetrahedron Lett. 2006, 47, 8679-8682.
28. (a) Dodda, R.; Goldman, J. J.; Mandal, T.; Zhao, C.-G.; Broker, G. A.; Tiekink, E. R. T. Adv. Synth. Cat. 2008, 350, 537-541;
29. (b) Wang, J.; Xie, H.; Li, H.; Zu, L.; Wang, W. Angew. Chem., Int. Ed. 2008, 47, 4177-4179.
30. Zu, L.; Wang, J.; Li, H.; Xie, H.; Jiang, W.; Wang, W. J. Am. Chem. Soc. 2007, 129, 1036-1037.
31. Zu, L.; Xie, H.; Li, H.; Wang, J.; Jiang, W.; Wang, W. Adv. Synth. Cat. 2007, 349, 1882-1886.
32. Dodda, R.; Mandal, T.; Zhao, C.-G. Tetrahedron Lett. 2008, 49, 1899-1902.
33. LiClO4 in Prins-cyclization: (a) Markert, M.; Buchem, I.; Kruger, H.; Mahrwald, R. Tetrahedron 2004, 60, 993-999
34. LiClO4 in aldol-Tischchenko reactions (b) Markert, M.; Mahrwald, R. Synthesis 2004, 1429-1433.
35. For reviews in this field see: (a) Sankararaman, S.; Nesakumar, J. E. Eur. J. Org. Chem. 2000, 2003-2011
36. (b) Deshpande, S. S.; Kumar, A. Adv. Org. Synth. 2005, 1, 215-232.
37. For results of this optimization-work see Supplementary data.