Reaction of vinylcarbenoids with thioketones: Formation of vinylthiocarbonyl ylides followed by ring closure to thiiranes and dihydrothiophenes

Tetrahedron Letters

Volumn 40, Issue 46, 1999, Pages 8117-8120

  Hamaguchi, Masashi ^a   Funakoshi, Nao ^a   Oshima, Takumi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Carbenes; Carbenoids; Cyclization; Thiocarbonyl compounds; Ylides

Indexed keywords

ALKENE; CARBONYL DERIVATIVE; SULFUR DERIVATIVE; THIOKETONE; THIOPHENE DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CYCLIZATION; DESULFURIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0033550248     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01716-5     Document Type: Article

References (28)

1. Schönberg, A.; König, B.; Singer, E. Chem. Ber. 1967, 100, 767.
2. (a) Huisgen, R.; Langhals, E. Tetrahedron Lett. 1989, 30, 5369.
3. (b) Huisgen, R.; Xingya, L. Tetrahedron Lett. 1983, 24, 4185.
4. (c) Huisgen, R.; Xingya, L. Heterocycle 1983, 20, 2363.
5. (d) Kalwinsch, I.; Xingya, L.; Gottstein, J.; Huisgen, R. J. Am. Chem. Soc. 1981, 703, 7032.
6. Mataka, S.; Ishi-i, S.; Tashiro, M. J. Org. Chem. 1978, 43, 3730.
7. (a) Kägi, M.; Linden, A.; Mloston, G.; Heimgartner, H. Helv. Chim. Acta. 1998, 81, 285.
8. (b) Mloston, G.; Heimgartner, H. Helv. Chim. Acta. 1996, 79, 1785.
9. (c) Kägi, M.; Linden, A.; Mloston, G.; Heimgartner, H. Helv. Chim. Acta. 1996, 79, 855.
10. (d) Mloston, G.; Petit, M.; Linden, A.; Heimgartner, H. Helv. Chim. Acta. 1994, 77, 435.
11. (a) Takano, S.; Tomita, S.; Takahashi, M.; Ogasawara, K. Synthesis 1987, 1116.
12. (b) Fang, F. G.; Prato, M.; Kim, G.; Danishefsky, S. J. Tetrahedron Lett. 1989, 30, 3625.
13. (c) Fang, F. G.; Danishefsky, S. J. Tetrahedron Lett. 1989, 30, 2747.
14. (d) Fang, F. G.; Maier, M. E.; Danishefsky, S. J. J. Org. Chem. 1990, 55, 831.
15. (e) Kim, G.; Chu-Moyer, M. Y; Danishefsky, S. J. J. Am. Chem. Soc. 1990, 112, 2003.
16. (f) Kim, G.; Chu-Moyer, M. Y; Danishefsky, S. J.; Shulte, G. K. J. Am. Chem. Soc. 1993, 115, 30.
17. (g) Mlostón, G.; Heimgartner, H. Helv. Chim. Acta. 1996, 79, 1785.
18. (a) Gu, H. H.; McDaniel, K. F.; McMills, M. C.; Yap, G. P; Rheingold, A. L. Tetrahedron Lett. 1997, 38, 6993.
19. (b) Davies, H. M. L.; Bruzinski, P. R.; Lake, D. H.; Kong, N.; Fall, M. J. J. Am. Chem. Soc. 1996, 118, 6897.
20. (c) Davies, H. M. L.; Doan, B. D. Tetrahedron Lett. 1996, 37, 3967.
21. (d) Davies, H. M. L.; Hansen, T.; Rutberg, J.; Bruzinski, P. R. Tetrahedron Lett. 1997, 38, 1741.
22. (e) Yoshikoshi, K.; Achiwa, K. Chem. Pharm. Bull. 1995, 43, 2048.
23. (a) Davies, H. M. L. Tetrahedron 1993, 49, 5203.
24. (b) Davies, H. M. L.; Doan, B. D. J. Org. Chem. 1998, 63, 657.
25. (c) Davies, H. M. L.; Clark, T. J. Tetrahedron 1994, 50, 9883.
26. Hamaguchi, M.; Misumi, T.; Oshima, T. Tetrahedron Lett. 1998, 39, 7113.
27. As the trans structure of α-cyanostyryl group was confirmed by NOE experiments, the suffixes E, Z are used to denote the stereochemistry of another double bond of the dienes.
28. 3) data for 9c: δ 5.85 (d, 1H, J=6.3 Hz), 5.96 (s, 1H), 6.68 (dd, 1H, J=8.5, 1.4 Hz), 6.80-6.86 (m, 1H), 6.89 (d, 1H, J=6.3), 7.05-7.14 (m, 5H), 7.30 (dd, 1H, J=7.9, 1.3 Hz), 7.45-7.48 (m, 3H), 7.62-7.66 (m, 2H).