Titanocene(ll)-promoted, one-pot, three-component coupling of thioacetals, alkynyl sulfones, and carbonyl compounds: Highly stereoselective formation of ferf-homopropargyl alcohols

Organic Letters

Volumn 9, Issue 15, 2007, Pages 2875-2878

  Takeda, Takeshi ^a   Ando, Maiko ^a   Sugita, Takenori ^a   Tsubouchi, Akira ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34547147897     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol071077w     Document Type: Article

References (31)

1. Ogata, A.; Nemoto, M.; Kobayashi, K.; Tsubouchi, A.; Takeda, T. Chem - Eur. J. 2007, 13, 1320-1325.
2. Takeda, T.; Shimokawa, H.; Miyachi, Y.; Fujiwara, T. Chem. Commun. 1997, 1055-1056.
3. (a) Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 2.
4. (b) Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293-1316.
5. (c) Marshall, J. A. Chem. Rev. 1996, 96, 31-47.
6. (d) Marshall, J. A. Chem. Rev. 2000, 100, 3163-3185.
7. (e) Marshall, J. A.; Gung, B. W.; Grachan, M. L. In Modern Allen Chemistry; Krause, N., Hashmi, A. S. K., Eds.; Wiley-VCH: Weinheim, 2004; Vol. 1, pp 493-592. For recent examples, see:
8. (f) Lai, C.; Soderquist, J. A. Org. Lett. 2005, 5, 799-802.
9. (g) Marshall, J. A.; Eidam, P.; Eidam, H. S. J. Org. Chem. 2006, 71, 4840-4844.
10. (h) Groth, U.; Kesenheimer, C.; Neidhöfer, J. Synlett 2006, 1859-1862.
11. (i) Hegedus, L. S.; Ranslow, P.; Achmatowicz, M.; de los Rios, C.; Hyland, C.; Gracia-Frutos, E. M.; Salman, S. Pure Appl. Chem. 2006, 78, 333-339.
12. (j)Vrancken, E.; Alouane, N.; Gérard, H.; Mangeney, P. J. Org. Chem. 2007, 72, 1770-1779 and references cited therein.
13. (a) Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-2227.
14. (b) Furuta, K.; Ishiguro, M.; Haruta, R.; Ikeda, N.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 2768-2776.
15. (a) Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835-2886.
16. (b) Yoshida, Y.; Nakagawa, T.; Sato, F. Synlett 1996, 437-438.
17. (c) Hanazawa, T.; Okamoto, S.; Sato, F. Org. Lett. 2000, 2, 2369-2371.
18. (d) Okamoto, S.; Matsuda, S.; An, D. K.; Sato, F. Tetrahedron Lett. 2001, 42, 6323-6326.
19. Yang, F.; Zhao, G.; Ding, Y. Tetrahedron Lett. 2001, 42, 2839-2841.
20. (a) Danheiser, R. L.; Carini, D. J.; Basak, A. J. Am. Chem. Soc. 1981, 103, 1604-1606.
21. (b) Danheiser, R. L.; Carini, D. J.; Fink, D. M.; Basak, A. Tetrahedron 1983, 39, 935-947.
22. (a) Yamamoto, Y. Acc. Chem. Res. 1987, 20, 243-249.
23. (b) Comprehensive Organic Synthesis, Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 1.
24. (c) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207-2293.
25. (d) Denmark, S. E.; Fu, J. Chem. Rev. 2003, 103, 2763-2793.
26. For recent example, see: (a) Yasuda, M.; Hirata, K.; Nishino, M.; Yamamoto, A.; Baba, A. J. Am. Chem. Soc. 2002, 124, 13442-13441.
27. (b) Wada, R.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 8910-8911.
28. (c) Wadamoto, M.; Yamamoto, H. J. Am. Chem. Soc. 2005, 127, 14556-14557.
29. (d) Lou, S.; Moquist, P. N.; Schaus, S. E. J. Am. Chem. Soc. 2006, 128, 12660-12661.
30. (e) Ren, H.; Dunet, G.; Mayer, P.; Knochel, P. J. Am. Chem. Soc. 2007, 129, 5376-5377.
31. Utimoto, K. Pure Appl. Chem. 1983, 55, 1845-1852.