BF3-promoted cyclization reaction of imines and salicylaldehyde with silyl enol ethers: unexpected formation of dioxaspiro compounds

Tetrahedron

Volumn 64, Issue 39, 2008, Pages 9315-9319

  Xin, Yong ^a   Jiang, Huiling ^a   Zhao, Jingwei ^a   Zhu, Shizheng ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ETHER DERIVATIVE; IMINE; SALICYLALDEHYDE; SILYL ENOL ETHER DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 49149114611     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.07.019     Document Type: Article

References (36)

1. For reviews, see:
2. Kobayashi S., and Ishitani H. Chem. Rev. 9 (1999) 1069-1094
3. Córdova A. Acc. Chem. Res. 37 (2004) 102-112
4. Marques M.M.B. Angew. Chem., Int. Ed. 45 (2006) 348-352
5. Ojima I., Inaba S., and Yoshida K. Tetrahedron Lett. 18 (1977) 3643-3646
6. Guanti G., Narisano E., and Banti L. Tetrahedron Lett. 28 (1987) 4331-4334
7. Mukaiyama T., Akamatsu H., and Han J.S. Chem. Lett. 19 (1990) 889-892
8. Onaka M., Ohno R., Yanagiya N., and Izumi Y. Synlett (1993) 141-142
9. Ishihara K., Funahashim K., Hanaki N., Miyata M., and Yamamoto H. Synlett (1994) 963-964
10. Ishihara K., Hanaki N., Hattori K., Tada T., and Yamamoto H. J. Am. Chem. Soc. 116 (1994) 10520-10524
11. Xue S., Yu S., Deng Y., and Wulff W.D. Angew. Chem., Int. Ed. 40 (2001) 2271-2274
12. Yamashita Y., Ueno M., Kuriyama Y., and Kobayashi S. Adv. Synth. Catal. 344 (2002) 929-931
13. Ueno M., Ishitani H., and Kobayashi S. Org. Lett. 4 (2002) 3395-3397
14. Kobayashi S., Kobayashi J., Ishitani H., and Ueno M. Chem.-Eur J. 8 (2002) 4185-4190
15. Trost B.M., and Terrell L.R. J. Am. Chem. Soc. 125 (2003) 338-339
16. Jaber N., Carrée F., Fiaud J.-C., and Collin J. Tetrahedron: Asymmetry 14 (2003) 2067-2071
17. Kobayashi S., Ueno M., Saito S., Mizuki Y., Ishitani H., and Yamashita Y. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 5476-5481
18. Josephsohn N.S., Snapper M.L., and Hoveyda A.H. J. Am. Chem. Soc. 126 (2004) 3734-3735
19. Josephsohn N.S., Carswell E.L., Snapper M.L., and Hoveyda A.H. Org. Lett. 7 (2005) 2711-2713
20. Ihori Y., Yamashita Y., Ishitani H., and Kobayashi S. J. Am. Chem. Soc. 127 (2005) 15528-15535
21. Cozzi P.G., and Rivalta E. Angew. Chem., Int. Ed. 44 (2005) 3600-3603
22. Kobayashi S., Matsubara R., and Kitagawa H. Org. Lett. 4 (2002) 143-145
23. Kobayashi S., Matsubara R., Nakamura Y., Kitagawa H., and Sugiura M. J. Am. Chem. Soc. 125 (2003) 2507-2515
24. Nakamura Y., Matsubara R., Kiyohara H., and Kobayashi S. Org. Lett. 5 (2003) 2481-2484
25. Matsunaga S., Yoshida T., Naoya M., Kumagai N., and Shibasaki M. J. Am. Chem. Soc. 126 (2004) 8777-8785
26. Trost B.M., Jaratjaroonphong J., and Reutrakul V. J. Am. Chem. Soc. 128 (2006) 2778-2779
27. Matsunaga S., Kumagai N., Harada S., and Shibasaki M. J. Am. Chem. Soc. 125 (2003) 4712-4713
28. Yoshida T., Morimoto H., Kumagai N., Matsunaga S., and Shibasaki M. Angew. Chem., Int. Ed. 44 (2005) 3470-3474
29. Sugita M., Yamaguchi A., Yamagiwa N., Handa S., Matsunaga S., and Shibasaki M. Org. Lett. 7 (2005) 5339-5343
30. Kise N., Ohya K., Arimoto K., Yamashita Y., Hirano Y., Ono T., and Ueda N. J. Org. Chem. 69 (2004) 7710-7719
31. Banphavichit V., Mansawat W., Bhanthumnavin W., and Vilaivan T. Tetrahedron 60 (2004) 10559-10568
32. Oi S., Moro M., Kawanishi T., and Inoue Y. Tetrahedron Lett. 45 (2004) 4855-4857
33. Ishimaru K., and Kojima T. J. Org. Chem. 68 (2003) 4959-4962
34. Jiang H.L., and Zhu S.Z. Synlett (2006) 1343-1346
35. Overman L.E., and Watson D.A. J. Org. Chem. 71 (2006) 2587-2599
36. Tripathi T. Inorg. Nucl. Chem. Lett. 14 (1978) 97-99