Photoreactions of β-aziridinylacrylonitriles and acrylates with alkenes: the substituent effects on the formation of [3+2] cycloadducts

Tetrahedron

Volumn 62, Issue 47, 2006, Pages 10865-10878

  Ishii, Keitaro ^a   Sone, Takuya ^a   Shigeyama, Takahide ^a   Noji, Masahiro ^a   Sugiyama, Shigeo ^a  

^a MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

3+2 Cycloaddition; Aziridine; Indolizidine; Photolysis; Pyrrolidine

Indexed keywords

1,3 BUTADIENE; ACRYLONITRILE; ALKENE DERIVATIVE; AZIRIDINE DERIVATIVE; AZIRINE DERIVATIVE; ESTER DERIVATIVE; OXYGEN; PYRROLE DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; CYCLOADDITION; ELECTRON; PHOTOCHEMISTRY; PHOTOREACTIVITY; PRIORITY JOURNAL;

EID: 33749526652     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.08.098     Document Type: Article

References (37)

1. For a review, see:
2. Lown W.J. In: Padwa A. (Ed). 1,3-Dipolar Cycloaddition Chemistry Vol. 1 (1984), Wiley, New York, NY
3. Pearson W.H., and Stoy P. Synlett (2003) 903-921
4. Coldham I., and Hufton R. Chem. Rev. 105 (2005) 2765-2809
5. Huisgen R., Scheer W., and Huber H. J. Am. Chem. Soc. 89 (1967) 1753-1755
6. DeShong P., Kell D.A., and Sidler D.R. J. Org. Chem. 50 (1985) 2309-2315
7. Eberbach W., Heinze I., Knoll K., Fritz H., and Borle F. Helv. Chim. Acta 71 (1988) 404-418
8. Henke B.R., Kouklis A.J., and Heathcock C.H. J. Org. Chem. 57 (1992) 7056-7066
9. Garner P., Cox P.B., Anderson J.T., Protasiewiez J., and Zaniewski R. J. Org. Chem. 62 (1997) 493-498
10. Gaebert C., and Mattay J. Tetrahedron 53 (1997) 14297-14316
11. Chen C., Li X., and Schreiber S.L. J. Am. Chem. Soc. 125 (2003) 10174-10175
12. Gao W., Zhang X., and Raghunath M. Org. Lett. 7 (2005) 4241-4244
13. Ishii K., Shimada Y., Sugiyama S., and Noji M. J. Chem. Soc., Perkin Trans. 1 (2000) 3022-3024
14. Ishii K., Sone T., Shimada Y., Shigeyama T., Noji M., and Sugiyama S. Tetrahedron 60 (2004) 10887-10898
15. Hirota H., Matsunaga S., and Fusetani N. Tetrahedron Lett. 31 (1990) 4163-4164
16. Shin J., Seo Y., Cho K.W., Rho J.-R., and Sim C.J. J. Nat. Prod. 60 (1997) 611-613
17. Whitlock G.A., and Carreira E.M. Helv. Chim. Acta 83 (2000) 2007-2022
18. Yamazaki N., Dokoshi W., and Kibayashi C. Org. Lett. 3 (2001) 193-196
19. Pilli R.A., Zanotto P.R., and Böckelmann M.A. Tetrahedron Lett. 42 (2001) 7003-7005
20. Davoli P., Moretti I., Prati F., and Alper H. J. Org. Chem. 64 (1999) 518-521
21. Andersson P.G., Guijarro D., and Tanner D. J. Org. Chem. 62 (1997) 7364-7375
22. Andrés J.M., de Elena N., Pedrosa R., and Pérez-Encabo A. Tetrahedron 55 (1999) 14137-14144
23. Ley S.V., and Middleton B. Chem. Commun. (1998) 1995-1996
24. Davoli P., Forni A., Moretti I., Prati F., and Torre G. Tetrahedron 57 (2001) 1801-1812
25. Wattanasin S., and Kathawala F.G. Synth. Commun. 22 (1992) 1487-1490
26. Hada K., Watanabe T., Isobe T., and Ishikawa T. J. Am. Chem. Soc. 123 (2001) 7705-7706
27. Coldham I., Collis A.J., Mould R.J., and Robinson D.E. Synthesis (1995) 1147-1150
28. Utsunomiya I., Fuji M., Sato T., and Natsume M. Chem. Pharm. Bull. 41 (1993) 854-860
29. Yields for compounds are based on converted starting material.
30. Åhman J., and Somfai P. Tetrahedron 55 (1999) 11595-11600
31. Sajimon M.C., Ramaiah D., Thomas K.G., and George M.V. J. Org. Chem. 66 (2001) 3182-3187
32. Kohmoto S., Kobayashi T., Minami J., Ying X., Yamaguchi T., Karatsu K., Kitamura A., Kishikawa K., and Yamamoto M. J. Org. Chem. 66 (2001) 66-73
33. Ciufolini M.A., Rivera-Fortin M.A., Zuzukin V., and Whitmire K.H. J. Am. Chem. Soc. 116 (1994) 1272-1277
34. Kotera M., Ishii K., Tamura O., and Sakamoto M. J. Chem. Soc., Perkin Trans. 1 (1994) 2353-2354
35. Kotera M., Ishii K., Tamura O., and Sakamoto M. J. Chem. Soc., Perkin Trans. 1 (1998) 313-318
36. Kotera M., Ishii K., Hiraga M., and Sakamoto M. Heterocycles 51 (1999) 2147-2157
37. Private information from Prof. Chihiro Kibayashi (Tokyo University of Pharmacy and Life Science).