Reaction of pyridine N-oxides with Grignard reagents: a stereodefined synthesis of substituted dienal oximes

Tetrahedron Letters

Volumn 48, Issue 39, 2007, Pages 6941-6944

  Andersson, Hans ^a   Wang, Xiaoyang ^a   Björklund, Mikael ^a   Olsson, Roger ^b   Almqvist, Fredrik ^a  

^a UMEÅ UNIVERSITY   (Sweden)

^b ACADIA Pharmaceuticals AB   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

OXIME; PYRIDINE 1 OXIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; GRIGNARD REACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 34548230025     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.07.161     Document Type: Article

References (33)

1. Zacharie B., Moreau N., and Dockendorff C. J. Org. Chem. 66 (2001) 5264-5265
2. Raminelli C., Lui Z., and Larock R.C. J. Org. Chem. 71 (2006) 4689-4691 (and references cited therein)
3. Campeau L.-C., Rousseaux S., and Fagnou K. J. Am. Chem. Soc. 127 (2005) 1820-1821
4. Stout D.M., and Meyers A.I. Chem. Rev. 82 (1982) 223-243
5. Laschat S., and Dickner T. Synthesis (2000) 1781-1813
6. Lavilla R. J. Chem. Soc., Perkin Trans. 1 (2002) 1141-1156
7. Wang X., Kauppi A.M., Olsson R., and Almqvist F. Eur. J. Org. Chem. (2003) 4586-4592
8. Charette A., Grenon M., Lemire A., Pourashraf M., and Martel J. J. Am. Chem. Soc. 123 (2001) 11829-11830
9. Ochiai E., and Arima K. J. Pharm. Soc. Jpn. 69 (1949) 51-54
10. Kato T., and Yamanaka H. J. Org. Chem. 30 (1965) 910-913
11. Kato T., Yamanaka H., Adachi T., and Hiranuma H. J. Org. Chem. 32 (1967) 3788-3790
12. Kellog R.M., and Van Bergen T. J. Org. Chem. 36 (1971) 1705-1708
13. Shiess P., and Ringele P. Tetrahedron Lett. (1972) 311-312
14. Shiess P., Monnier C., Ringele P., and Sendi E. Helv. Chim. Acta 57 (1974) 1676-1691
15. Coperet C., Adolfsson H., Khuong T.-A.V., Yudin A.K., and Sharpless K.B. J. Org. Chem. 63 (1998) 1740-1741
16. Caron S., Do N.M., and Sieser J.E. Tetrahedron Lett. 41 (2000) 2299-2302
17. Youssif S. ARKIVOC 2 (2001) 242-268
18. Winkeljohn W.R., Vasquez P.C., Strekowski L., and Baumstark A.L. Tetrahedron Lett. 45 (2004) 8295-8297
19. Vilsmeier A., and Haack A. Chem. Ber. 60 (1927) 119-122
20. Andersson H., Almqvist F., and Olsson R. Org. Lett. 9 (2007) 1335-1337
21. McCarty C.G. In: Patai S. (Ed). The Chemistry of the Carbon-Nitrogen Double Bond (1970), Interscience, Newyork, NY 363-464
22. Searcey M., Grewal S.S., Madeo T., and Tsoungas P.G. Tetrahedron Lett. 44 (2003) 6745-6747
23. Couturier M., Tucker J.L., Andresen B.M., Dube P., Brenek S.J., and Negri J.T. Tetrahedron Lett. 42 (2001) 2285-2288
24. Gribble G.W. Chem. Soc. Rev. 27 (1998) 395-404
25. Wang S.S., and Sukenik C.N. J. Org. Chem. 50 (1985) 5448-5450
26. Feuer H., and Braunstein D.M. J. Org. Chem. 34 (1969) 1817-1821
27. Hatanaka M., and Ishimaru T. J. Med. Chem. 16 (1973) 978-984
28. Cunha S., Rodovaho W., Azevedo N.R., Mendonca M.D.O., Lariucci C., and Vencato I. J. Braz. Chem. Soc. 13 (2002) 629-634
29. Kascheres C.M. J. Braz. Chem. Soc. 14 (2003) 945-969
30. Katritzky A.R., Hayden A.E., Kirichenko K., Pelphrey P., and Ji Y. J. Org. Chem. 69 (2004) 5108-5111
31. Singh V., Saxena R., and Batra S. J. Org. Chem. 70 (2005) 353-356
32. Missio L.J., Braibante H.S., and Braibante M.E.F. J. Heterocyl. Chem. 33 (1996) 1243-1245
33. Kreich M., and Claus P. Angew. Chem., Int. Ed. 44 (2005) 7800-7804