Formal (3+3) cycloaddition of silyl enol ethers catalyzed by trifric imide: Domino michael addition-claisen condensation accompanied with isomerization of silyl enol ethers

Chemical and Pharmaceutical Bulletin

Volumn 59, Issue 9, 2011, Pages 1190-1193

  Azuma, Takumi ^a   Takemoto, Yoshiji ^a   Takasu, Kiyosei ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

(3+3) cycloaddition; Domino reaction; Silyl enol ether; Triflic imide

Indexed keywords

ACRYLIC ACID DERIVATIVE; IMIDE; SILANE DERIVATIVE; TRIFLIC IMIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CLAISEN CONDENSATION; CYCLOADDITION; ISOMERIZATION; MICHAEL ADDITION; PROTON NUCLEAR MAGNETIC RESONANCE;

CATALYSIS; CYCLIZATION; ETHERS; MESYLATES; SILICON; STEREOISOMERISM;

EID: 80052283477     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.59.1190     Document Type: Article

References (24)

1. Magnus P., Mugrage B., J. Am. Chem. Soc., 112, 462-464 (1990).
2. Magnus P., Coldham I., J. Am. Chem. Soc., 113, 672-673 (1991).
3. Magnus P., Rigollier P., Lacour J., Tobler H., J. Am. Chem. Soc., 115, 12629-12630 (1993).
4. Kuwajima I., Shoda H., Nakamura T., Tanino K., Tetrahedron Lett., 34, 6281-6284 (1993).
5. Ruck R. T., Jacobsen E. N., Angew. Chem. Int. Ed., 42, 4771-4774 (2003).
6. Bellur E., Görls H., Langer P., J. Org. Chem., 70, 4751-4761 (2005).
7. Kuwajima I., Horiguchi Y., Nakamura E., Tetrahedron Lett., 30, 3323-3326 (1989).
8. Mikami K., Ohmura H., Chem. Commun. (Cambridge), 2002, 2626-2627 (2002).
9. He J., Tchabanenko K., Adlington R. M., Cowley A. R., Baldwin J. E., Eur. J. Org. Chem., 4003-4013 (2006).
10. Kusama H., Yamabe H., Iwasawa N., Org. Lett., 4, 2569-2571 (2002).
11. Inanaga K., Takasu K., Ihara M., J. Am. Chem. Soc., 127, 3668-3669 (2005).
12. Takasu K., Ishii T., Inanaga K., Ihara M., Org. Synth., 83, 193-199 (2006).
13. Takasu K., Miyakawa Y., Ihara M., Tokuyama H., Chem. Pharm. Bull., 56, 1205-1206 (2008).
14. Takasu K., Synlett, 2009, 1905-1914 (2009).
15. Takasu K., Ueno M., Inanaga K., Ihara M., J. Org. Chem., 69, 517-521 (2004).
16. We have reported that retro (2+2) cycloaddition undergoes in the presence of acid catalysts at ambient temperature. See Takasu K., Ueno M., Ihara M., J. Org. Chem., 66, 4667-4672 (2001).
17. Takasu K., Inanaga K., Ihara M., Tetrahedron Lett., 49, 4220-4222 (2008).
18. Only a limited number of acid-catalyzed Claisen condensation of silyl enol ethers have been reported. See refs. 19-21.
19. Onaka M., Mimura T., Ohno R., Izumi Y., Tetrahedron Lett., 30, 6341-6344 (1989).
20. Iwata S., Hamura T., Matsumoto T., Suzuki K., Chem. Lett., 36, 538-539 (2007).
21. Ondrus A. E., Kaniskan H. U., Movassaghi M., Tetrahedron, 66, 4784-4795 (2010).
22. Barton D. H. R., Nickson A., J. Chem. Soc., 4665-4669 (1954).
23. As a first total synthesis of clovane:Kundu A. K., Kundu N. G., Dutta P. C., J. Chem. Soc., 1965, 2749-2763 (1965).
24. Shindoh N., Takemoto Y., Takasu K., Chem. Eur. J., 15, 12168-12179 (2009).