GaCI3- and TiCl4-catalyzed insertion of isocyanides into a C-S bond of dithioacetals

Organic Letters

Volumn 10, Issue 22, 2008, Pages 5223-5225

  Tobisu, Mamoru ^a   Ito, Sana ^a   Kitajima, Aki ^a   Chatani, Naoto ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

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Indexed keywords

EID: 61349187595     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802223a     Document Type: Article

References (32)

1. Selected reviews: (a) Bulman Page, P. C.; van Niel, M. B.; Prodger, J. C. Tetrahedron 1989, 45, 7643.
2. (b) Luh, T.-Y. Acc. Chem. Res. 1991, 24, 257-263.
3. (c) Luh, T.-Y.; Lee, C.-F. Eur. J. Org. Chem. 2005, 3875.
4. (d) Takeda, T. Bull. Chem. Soc. Jpn, 2005, 78, 195.
5. Gröbel, B.-T.; Seebach, D. Synthesis 1977, 357.
6. (a) Nakamura, I.; Bajracharya, G. B.; Wu, H.; Oishi, K.; Mizushima, Y.; Gridnev, I. D.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 15423.
7. (b) Peng, L.; Zhang, X.; Zhang, S.; Wang, J. J. Org. Chem. 2007, 72, 1192.
8. See also (c) Nakamura, I.; Sato, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2006, 45, 4473.
9. (d) Nakamura, I.; Sato, T.; Terada, M.; Yamamoto, Y. Org. Lett. 2007, 9, 4081.
10. (e) Nakamura, I.; Sato, T.; Terada, M.; Yamamoto, Y. Org. Lett. 2008, 10, 2649.
11. Intermolecular insertion of CO into the C-S bond of N,S-acetals has been reported: Khumtaveeporn, K.; Alper, H. J. Org. Chem 1994 59 1414.
12. (a) Chatani, N.; Oshita, M.; Tobisu, M.; Ishii, Y.; Murai, S. J. Am. Chem. Soc. 2003, 125, 7812.
13. (b) Oshita, M.; Yamashita, K.; Tobisu, M.; Chatani, N. J. Am. Chem. Soc. 2005, 127, 761.
14. (c) Yoshioka, S.; Oshita, M.; Tobisu, M.; Chatani, N. Org. Lett. 2005, 7, 3697.
15. (d) Tobisu, M.; Oshita, M.; Yoshioka, S.; Kitajima, A.; Chatani, N. Pure Appl. Chem. 2006, 78, 275.
16. (e) Tobisu, M.; Kitajima, A.; Yoshioka, S.; Hyodo, I.; Oshita, M.; Chatani, N. J. Am. Chem. Soc. 2007, 129, 11431.
17. (f) Tobisu, M.; Yamaguchi, S.; Chatani, N. Org. Lett. 2007, 9, 3351.
18. For the gallium-mediated cleavage of the C-S bond in dithioacetals, see: (a) Saigo, K.; Hashimoto, Y.; Kihara, N.; Umehara, H.; Hasegawa, M. Chem. Lett. 1990, 19, 831.
19. (b) Saigo, K.; Hashimoto, Y.; Kihara, N.; Kara, K.; Hasegawa, M. Chem. Lett. 1990, 19, 1097.
20. (c) Ikeshita, K.; Kihara, N.; Ogawa, A. Tetrahedron Lett. 2005, 46, 8773.
21. (d) Ikeshita, K.; Kihara, N.; Sonoda, M.; Ogawa, A. Tetrahedron Lett. 2007, 48, 3025.
22. Notes: (a) The results when isocyanides other than 2 were used are as follows. 2,6-Dimethylphenyl isoeyanide: 3 (31%), 4 (26%). 2,6-Diisopropylphenyl isoeyanide: 3 (41%), 4 (18%). tert-Octyl isoeyanide: 3 (0%), 4 (0%). (b) Diphenylthioacetals and 1,3-dithiolane did not give any insertion products.
23. Similar effect of a tert-butyl group was also observed in the insertion into acetals. See refs 5c and 5d.
24. 2 = 6.9:1:0.4.
25. 4.
26. 3 resulted in a complete scrambling of the alkylthio groups between the starting meterials. This observation indicates the involvement of free metal-thiolate species, as in C, rather than involving an intimate ion pair.
27. For reviews, see: (a) Ogawa, A.; Sonoda, N. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon: Oxford, 1995; Vol. 5 (Moody, C. J., Ed.), p 233.
28. (b) Fujiwara, S.; Kambe, N. Top. Curr. Chem. 2005, 251, 87.
29. For recent reports on catalytic transformation of thioesters, see: (a) Villalobos, J. M.; Srogl, J.; Liebeskind, L. S. J. Am. Chem. Sac. 2007, 129, 15734.
30. (b) Yang, H.; Li, H.; Wittenberg, R.; Egi, M.; Huang, W.; Liebeskind, L. S. J. Am. Chem. Soc. 2007, 129, 1132.
31. (c) Yamashita, F.; Kuniyasu, H.; Terao, J.; Kambe, N. Org. Lett. 2008, 10, 101.
32. (d) Li, H.; Yang, H.; Liebeskind, L. S. Org. Lett. 2008, 10, 4375.