Facile isomerization of silyl enol ethers catalyzed by triflic imide and its application to one-pot isomerization-(2 + 2) cycloaddition

Beilstein Journal of Organic Chemistry

Volumn 8, Issue , 2012, Pages 658-661

  Inanaga, Kazato ^a   Ogawa, Yu ^b   Nagamoto, Yuuki ^b   Daigaku, Akihiro ^a   Tokuyama, Hidetoshi ^a   Takemoto, Yoshiji ^b   Takasu, Kiyosei ^b  

^a TOHOKU UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

Isomerization; One pot reaction; Organocatalysis; Silyl enol ethers; Triflic imide

Indexed keywords

EID: 84860620491     PISSN: None     EISSN: 18605397     Source Type: Journal    
DOI: 10.3762/bjoc.8.73     Document Type: Article

References (18)

1. Brownbridge, P. Synthesis 1983, 1-28. doi:10.1055/s-1983-30204
2. Brownbridge, P. Synthesis 1983, 85-104. doi:10.1055/s-1983-30234
3. Poirier, J.-M. Org. Prep. Proced. Int. 1988, 20, 317-369. doi:10.1080/00304948809355878
4. Stork, G.; Hudrlik, P. F. J. Am. Chem. Soc. 1968, 90, 4462-4464. doi:10.1021/ja01018a051
5. Deyine, A.; Dujardin, G.; Mammeri, M.; Poirier, J.-M. Synth. Commun. 1998, 28, 1817-1821. doi:10.1080/00397919808007012
6. Ishihara, K.; Nakamura, H.; Nakamura, S.; Yamamoto, H. J. Org. Chem. 1998, 63, 6444-6445. doi:10.1021/jo9812936
7. Aikawa, H.; Kaneko, T.; Asao, N.; Yamamoto, Y. Beilstein J. Org. Chem. 2011, 7, 648-652. doi:10.3762/bjoc.7.76
8. Takasu, K. Synlett 2009, 1905-1914. doi:10.1055/s-0029-1217522
9. Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Synlett 2001, 1851-1854. doi:10.1055/s-2001-18761
10. Inanaga, K.; Takasu, K.; Ihara, M. J. Am. Chem. Soc. 2005, 127, 3668-3669. doi:10.1021/ja042661s (Pubitemid 40411386)
11. Boxer, M. B.; Yamamoto, H. J. Am. Chem. Soc. 2006, 128, 48-49. doi:10.1021/ja054725k (Pubitemid 43100842)
12. Takasu, K.; Miyakawa, Y.; Ihara, M.; Tokuyama, H. Chem. Pharm. Bull. 2008, 56, 1205-1206. doi:10.1248/cpb.56.1205
13. Kurahashi, K.; Takemoto, Y.; Takasu, K. ChemSusChem 2012, 5, 270-273. doi:10.1002/cssc.201100373
14. Fogg, D. E.; dos Santos, E. N. Coord. Chem. Rev. 2004, 248, 2365-2379. doi:10.1016/j.ccr.2004.05.012
15. Shindoh, N.; Takemoto, Y.; Takasu, K. Chem.-Eur. J. 2009, 15, 12168-12179. doi:10.1002/chem.200901486
16. Shindoh, N.; Tokuyama, H.; Takemoto, Y.; Takasu, K. J. Org. Chem. 2008, 73, 7451-7456. doi:10.1021/jo8009243
17. Takasu, K.; Tanaka, T.; Azuma, T.; Takemoto, Y. Chem. Commun. 2010, 46, 8246-8248. doi:10.1039/c0cc03336g
18. Azuma, T.; Takemoto, Y.; Takasu, K. Chem. Pharm. Bull. 2011, 59, 1190-1193. doi:10.1248/cpb.59.1190