One-pot syntheses of 2,3-dihydrothiopyran-4-one derivatives by Pd/Cu-catalyzed reactions of α,β-unsaturated thioesters with propargyl alcohols

Organic Letters

Volumn 10, Issue 12, 2008, Pages 2469-2472

  Minami, Yasunori ^a   Kuniyasu, Hitoshi ^a   Kambe, Nobuaki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 49549111864     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800754w     Document Type: Article

References (37)

1. (a) Osakada, K.; Yamamoto, T.; Yamamoto, A. Tetrahedron Lett. 1987, 28, 6321.
2. (b) Kato, T.; Kuniyasu, H.; Kajiura, T.; Minami, Y.; Ohtaka, A.; Kinomoto, M.; Terao, J.; Kurosawa, H.; Kambe, N. Chem. Commun. 2006, 868.
3. (a) Fukuyama, T.; Lin, S.-C.; Li, L. J. Am. Chem. Soc. 1990, 112, 7050.
4. (b) Kuniyasu, H.; Ogawa, A.; Sonoda, N. Tetrahedron Lett. 1993, 34, 2491.
5. (a) Tokuyama, H.; Yokoshima, S.; Yamashita, T.; Fukuyama, T. Tetrahedron Lett. 1998, 39, 3189.
6. (b) Tokuyama, H.; Miyazaki, T.; Yokoshima, S.; Fukuyama, T. Synlett 2003, 1512.
7. (a) Liebeskind, L. S.; Srogl, J. J. Am. Chem. Soc. 2000, 122, 11260.
8. (b) Wittenberg, R.; Srogl, J.; Egi, M.; Liebeskind, L. S. Org. Lett. 2003, 5, 3033.
9. (c) Yang, H.; Li, H.; Wittenberg, R.; Egi, M.; Huang, W.; Liebeskind, L. S. J. Am. Chem. Soc. 2007, 129, 1132.
10. (d) Yang, H.; Liebeskind, L. S. Org. Lett. 2007, 9, 2993.
11. (e) Villalobos, J. M.; Srogl, J.; Liebeskind, L. S. J. Am. Chem. Soc. 2007, 129, 15734.
12. (a) Ikeda, Z; Hirayama, H.; Matsubara, S. Angew. Chem., Int. Ed. 2006, 45, 8200.
13. (b) Ooguri, A.; Ikeda, Z.; Matsubara, S. Chem. Commun. 2007, 4761.
14. (a) Kuniyasu, H.; Kurosawa, H. Chem. Eur. J. 2002, 8, 2660.
15. (b) Sugoh, K.; Kuniyasu, H.; Sugae, T.; Ohtaka, A.; Takai, Y.; Tanaka, A.; Machino, C.; Kambe, N.; Kurosawa, H. J. Am. Chem. Soc. 2001, 123, 5108.
16. (c) Hirai, T.; Kuniyasu, H.; Kambe, N. Chem. Lett. 2004, 33, 1148.
17. (d) Hirai, T.; Kuniyasu, H.; Kambe, N. Tetrahedron Lett. 2005, 46, 117.
18. (e) Hirai, T.; Kuniyasu, H.; Asano, S.; Terao, J.; Kambe, N. Synlett 2005, 1161.
19. (f) Kuniyasu, H.; Yamashita, F.; Hirai, T.; Ye, J.-H.; Fujiwara, S.; Kambe, N. Organometallics 2006, 25, 566.
20. (g) Kuniyasu, H.; Kambe, N. Chem. Lett. 2006, 35, 1320.
21. (h) Yamashita, F.; Kuniyasu, H.; Terao, J.; Kambe, N. Org. Lett. 2008, 10, 101.
22. (a) Ingall, A. H. In Comprehensive Heterocyclic Chemistry II; Boulton, A. S., McKkillop, A., Eds.; Pergamon Press: Oxford, 1996; Vol. 5, p 501.
23. (b) Schneller, S. W. Adv. Heterocycl. Chem. 1975, 18, 59.
24. (c) Katrizky, A. R.; Bonlton, A. J. Adv. Heterocycl. Chem. 1975, 18, 76.
25. (d) Al-Nakib, T.; Bezjak, V.; Meegan, M.; Chandy, R. Eur. J. Med. Chem. 1990, 25, 455.
26. (e) Al-Nakib, T.; Bezjak, V.; Rashid, S.; Fullam, B.; Meegan, M. Eur. J. Med. Chem. 1991, 26, 221.
27. (f) van Vliet, L. A.; Rodenhuis, N.; Dijkstra, D.; Wikstrom, H.; Pugsley, T. A.; Serpa, K. A.; Meltzer, L. T.; Heffner, T. G.; Wise, L. D.; Lajiness, M. E.; Huff, R. M.; Svensson, K.; Sundell, S.; Lundmark, M. J. Med. Chem. 2000, 43, 2871.
28. w = 0.184. See Supporting Informaion for crystal data for 3a. (9) The NOE experiment showed that the cis-isomer was exclusively produced. See Supporting Information for more details.
29. For addition of thiol to eynone, see: (a) Perlmutter, P. In Conjugate Addition Reactions in Organic Synthesis; Baldwin, J. E., Magnus, P. D., Eds.; Pergamon Press: Oxford, U.K., 1992; Vol. 9, pp 310-322.
30. (b) Blanco, L.; Bloch, R.; Bugnet, E.; Deloisy, S. Tetrahedron Lett. 2000, 41, 7875.
31. (c) Gardiner, J. M.; Giles, P. E.; Martin, M. L. M. Tetrahedron Lett. 2002, 43, 5415.
32. (d) Maezaki, N.; Yagi, S.; Yoshigami, R.; Maeda, J.; Suzuki, T.; Ohsawa, S.; Tsukamoto, K.; Tanaka, T. J. Org. Chem. 2003, 68, 5550.
33. (e) Hollowood, C. J.; Yamanoi, S.; Ley, S. V. Org. Biomol. Chem. 2003, 1, 1664.
34. (f) Ding, F.; Jennings, M. P. Org. Lett. 2005, 7, 2321.
35. For copper-catalyzed acylselenation and telluration of alkynes, see: (a) Zhao, C.-Q.; Huang, X.; Meng, J.-B. Tetrahedron Lett. 1998, 39, 1933.
36. (b) Zhao, C.-Q.; Li, J.-L.; Meng, J.-B.; Wang, Y.-M. J. Org. Chem. 1998, 63, 4170.
37. It has been reported that 2-arylthio-pyridine undergoes nucleophilic substitution by phenol: (a) Inoue, S. Phosphorus Sulfur 1985, 22, 141.