A novel class of azatricyclononanes: pentasubstituted cyclopropanes from an uncatalysed reaction

Tetrahedron Asymmetry

Volumn 20, Issue 6-8, 2009, Pages 726-729

  Harris, Lawrence ^a,b   Gilpin, Martin ^a,b   Thompson, Amber L ^a,b   Cowley, Andrew R ^a,b   Moloney, Mark G ^a,b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE DERIVATIVE; AZO COMPOUND; CYCLOPROPANE DERIVATIVE; PYROGLUTAMIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLOPROPANATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 65549164598     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.02.037     Document Type: Article

References (30)

1. Dyer J., Keeling S., King A., and Moloney M.G. J. Chem. Soc., Perkin Trans. 1 (2000) 2793-2804
2. Byfield A., Davis P., Foster A., and Moloney M.G. J. Chem. Soc., Perkin Trans. 1 (2000) 1977-1982
3. Bailey J.H., Cherry D., Dyer J., Moloney M.G., Bamford M.J., Keeling S., and Lamont R.B. J. Chem. Soc., Perkin Trans. 1 (2000) 2783-2792
4. Bailey J.H., Cherry D.T., Crapnell K.M., Moloney M.G., Shim S.B., Bamford M., and Lamont R.B. Tetrahedron 53 (1997) 11731-11744
5. Beard M.J., Bailey J.H., Cherry D.T., Moloney M.G., Shim S.B., Statham K., Bamford M., and Lamont R.B. Tetrahedron 52 (1996) 3719-3740 and corrigenda 1997, 53, 1177
6. Cottrell I.F., Davis P.J., and Moloney M.G. Tetrahedron: Asymmetry 15 (2004) 1239-1242
7. Bentz E.L., Goswami R., Moloney M.G., and Westaway S.M. Org. Biomol. Chem. 3 (2005) 2872-2882
8. Chan P.W.H., Cottrell I.F., and Moloney M.G. J. Chem. Soc., Perkin Trans. 1 (2001) 2997-3006
9. Chan P.W.H., Cottrell I.F., and Moloney M.G. J. Chem. Soc., Perkin Trans. 1 (2001) 3007-3012
10. Goswami R., and Moloney M.G. Chem. Commun. (1999) 2333-2334
11. Anwar M., Bailey J.H., Dickinson L., Edwards H., Goswami R., and Moloney M.G. Org. Biomol. Chem. 1 (2003) 2364-2376
12. Hill T., Kocis P., and Moloney M.G. Tetrahedron Lett. 47 (2006) 1461-1463
13. Fowden L., Smith A., Millington D.S., and Sheppard R.C. Phytochemistry (1969) 437-443
14. Hendrata S., Bennett F., Huang Y., Sannigrahi M., Pinto P.A., Chan T.-M., Evans C.A., Osterman R., Buevicha A., and McPhail A.T. Tetrahedron Lett. 47 (2006) 6469-6472
15. Brackmann F., Colombo N., Cabrele C., and Meijere A.D. Eur. J. Org. Chem. (2006) 4440-4450
16. Yohannes D., Procko K., Lebel L.A., Fox C.B., and O'Neill B.T. Bioorg. Med. Chem. Lett. 18 (2008) 2316-2319
17. Komine T., Kojima A., Asahina Y., Saito T., Takano H., Shibue T., and Fukuda Y. J. Med. Chem. 51 (2008) 6558-6562
18. Zhang R., Brownewell F., and Madalengoitia J.S. Tetrahedron Lett. 40 (1999) 2707-2710
19. Zhang R., Mamai A., and Madalengoitia J.S. J. Org. Chem. 64 (1999) 547-555
20. Zhang R., and Madalengoitia J.S. J. Org. Chem. 64 (1999) 330-331
21. Zhang R., Brownewell F., and Madalengoitia J.S. J. Am. Chem. Soc. 120 (1998) 3894-3902
22. Flemer S., Wurthmann A., Mamai A., and Madalengoitia J.S. J. Org. Chem. 73 (2008) 7593-7602
23. 2 and heated at reflux. After completion, the reaction mixture was concentrated and purified by column chromatography.
24. 29 and refined using the CRYSTALS software suite. Crystallographic data (excluding structure factors) for all structures have been deposited with the Cambridge Crystallographic Data Centre (CCDC 718621-718628) and copies of these data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif.
25. Trost B.M., and Crawley M.L. J. Am. Chem. Soc. 124 (2002) 9328-9329
26. Nakano Y., Hamaguchi M., and Nagai T. J. Org. Chem. 54 (1989) 1135-1144
27. Bennett P., Harwood L.M., Macro J., and McGregor A. Chem. Commun. (1994) 961-962
28. Altomare A., Cascarano G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori G., and Camalli M. J. Appl. Crystallogr. 27 (1994) 435
29. Betteridge P.W., Carruthers J.R., Cooper R.I., Prout K., and Watkin D.J. J. Appl. Crystallogr. 36 (2003) 1487
30. Best D., Jenkinson S.F., Rule S.D., Higham R., Mercer T.B., Newell R.J., Weymouth-Wilson A.C., Fleet G.W.J., and Petursson S. Tetrahedron Lett. 49 (2008) 2196-2199