8-Azabicyclo[3.2.1]oct-3-en-2-ones via asymmetric 1,3-dipolar cycloaddition of a homochiral 3-oxidopyridinium betaine

Tetrahedron Letters

Volumn 47, Issue 15, 2006, Pages 2635-2638

  Curtis, Neil R ^a   Ball, Richard G ^b   Kulagowski, Janusz J ^a  

^a NEUROSCIENCE RESEARCH CENTRE   (United Kingdom)

^b MERCK RESEARCH LABORATORIES   (United States)

Author keywords

1,3 Dipolar cycloaddition; 3 Oxidopyridinium betaine; 8 Azabicyclo 3.2.1 oct 3 en 2 one; Asymmetric synthesis; Diastereoselective; X ray crystallography

Indexed keywords

8 AZABICYCLO[3.2.1]OCT 3 EN 2 ONE DERIVATIVE; BETAINE; BICYCLO COMPOUND; PYRIDINIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; CYCLOADDITION; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; X RAY DIFFRACTION;

EID: 33644906123     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.02.005     Document Type: Article

References (19)

1. A.R. Katritzky, and N. Dennis Chem. Rev. 89 1989 827 861
2. P.-H. Ducrot, and J.Y. Lallemand Tetrahedron Lett. 31 1990 3879 3882
3. M.E. Jung, Z. Longmei, P. Tangsheng, Z. Huiyan, L. Yan, and S. Jingyu J. Org. Chem. 57 1992 3528 3530
4. A.P. Kozikowski, G.L. Araldi, and R.G. Ball J. Org. Chem. 62 1997 503 509
5. F. Estour, S. Rézel, D. Fraisse, J. Métin, V. Gaumet, C. Lartigue, G. Miscoria, A. Gueiffier, Y. Blache, J.C. Teulade, and O. Chavignon Heterocycles 50 1999 929 945
6. Curtis, N. R.; Kulagowski, J. J.; Huscroft, I. T.; Raubo, P. A. US 20020193402, 2002.
7. Chem. Abstr. 138 2002 39444
8. K.V. Gothelf, and K.A. Jørgensen Chem. Rev. 98 1998 863 909
9. T. Takahashi, K. Kitano, T. Hagi, H. Nihonmatsu, and T. Koizumi Chem. Lett. 1989 597 598
10. T. Takahashi, A. Fujii, J. Sugita, T. Hagi, K. Kitano, Y. Arai, T. Koizumi, and M. Shiro Tetrahedron: Asymmetry 2 1991 1379 1390
11. G.L. Araldi, K.R.C. Prakash, C. George, and A.P. Kozikowski Chem. Commun. 1997 1875 1876
12. K.R.C. Prakash, M. Trzcinska, K.M. Johnson, and A.P. Kozikowski Bioorg. Med. Chem. Lett. 10 2000 1443 1446
13. V.C. Pham, and J.L. Charlton J. Org. Chem. 60 1995 8051 8055
14. T. Shinohara, A. Takeda, J. Toda, N. Terasawa, and T. Sano Heterocycles 46 1997 555 566
15. C. Müller, V. Diehl, and F.W. Lichtenthaler Tetrahedron 54 1998 10703 10712
16. -3 and this peak is without chemical significance. Crystallographic data (excluding structure factors) have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 287235. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (0) 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk ].
17. 1a.
18. 3).
19. 3).