Reaction of functionalized azomethine ylides with olefinic dipolarophiles

Heterocycles

Volumn 70, Issue , 2006, Pages 647-654

  Kawashima, Keisuke ^a   Kahehi, Akikazu ^b   Noguchi, Michihiko ^a  

^a YAMAGUCHI UNIVERSITY GRADUATE SCHOOL OF MEDICINE   (Japan)

^b SHINSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33947672466     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-06-s(w)60     Document Type: Article

References (9)

1. Obst U., Betschmann P., Lemer C., Seiler P., and Diederich F. Helv. Chim. Acta 83 (2000) 855
2. Pearson W.H. In: Atta-Ur-Rahman (Ed). Studies in Natural Products Chemistry Vol. 1 (1998), Elsevier, New York 323-358
3. Gribble G.W. In: Katritzky A.R., Rees C.W., and Scriven E.F.V. (Eds). Comprehensive Heterocyclic Chemistry Vol. 2 (1996), Pergamon, Oxford, U. K. 207-257
4. Shirai M., Kuwabara H., Matsumoto S., Yamamoto H., Kakehi A., and Noguchi M. Tetrahedron 59 (2003) 4113
5. Noguchi M., Matsumoto S., Shirai M., and Yamamoto H. Tetrahedron 59 (2003) 4123
6. K. Kawashima, A. Kakehi, and M. Noguchi submitted to Tetrahedron.
7. The structures of cycloadducts (5, 6 and 7) were characterized by their spectroscopic data. Moreover, the structures of five key cycloadducts (5b, 7b, 5e, 6d and 6e) were confirmed by single crystal X-Ray analysis and crystallographic data have been deposited with Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 622532 for 5b, CCDC 622531 for 7b, CCDC 622529 for 5c, CCDC 622530 for 6d and CCDC 622533 for 6e. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
8. The calculation results of the dipoles of (E,E)-3 and (E,Z)-3 by PM3 indicated that the interconversion between these dipoles could be ruled out.
9. The general experimental procedures were the same as those reported in lit.4.