Extended pummerer reaction of arylketene dithioacetal monoxides with aromatic compounds by means of trifluoromethanesulfonic anhydride

Chemistry Letters

Volumn 37, Issue 7, 2008, Pages 786-787

  Yoshida, Suguru ^a   Yorimitsu, Hideki ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 49149120184     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2008.786     Document Type: Article

References (15)

1. S. K. Bur, A. Padwa, Chem. Rev. 2004, 104, 2401.
2. Application of the Pummerer reaction to synthesis of complex carbocycles and heterocycles has been shown: A. Padwa, D. E. Gunn, Jr., M. H. Osterhout, Synthesis 1997, 1353.
3. Selected examples: a) D. Craig, K. Daniels, Tetrahedron 1993, 49, 11263.
4. b) Y. Kita, Y. Takeda, M. Matsugi, K. Iio, K. Gotanda, K. Murata, S. Akai, Angew. Chem., Int. Ed. Engl. 1997, 36, 1529.
5. c) A. Padwa, J. T. Kuethe, J. Org. Chem. 1998, 63, 4256.
6. d) S. Akai, N. Morita, K. Iio, Y. Nakamura, Y. Kita, Org. Lett. 2000, 2, 2279.
7. e) K. S. Feldman, D. B. Vidulova, Org. Lett. 2004, 6, 1869.
8. f) S. Akai, N. Kawashita, H. Satoh, Y. Wada, K. Kakiguchi, I. Kuriwaki, Y. Kita, Org. Lett. 2004, 6, 3793.
9. g) A. Padwa, S. Nara, Q. Wang, Tetrahedron Lett. 2006, 47, 595.
10. S. Yoshida, H. Yorimitsu, K. Oshima, Org. Lett. 2007, 9, 5573.
11. 2O and its applications have been summarized: I. L. Baraznenok, V. G. Nenajdenko, E. S. Balenkova, Tetrahedron 2000, 56, 3077.
12. N2′ mode cannot be excluded.
13. 2 gave a complex mixture. After extensive screening of the reaction conditions for the cyclization, we have found the conditions.
14. For review on the Wagner-Meerwein rearrangement see: A. J. Floyd, S. F. Dyke, S. E. Ward, Chem. Rev. 1976, 76, 509.
15. Skeletal rearrangement to phenanthrenes from fluorenes by the Wagner-Meerwein rearrangement has been reported: W. G. Brown, B. J. Bluestein, J. Am. Chem. Soc. 1940, 62, 3256.