Synthesis of new tropinone derivatives by palladium-catalyzed couplings of 8-azabicyclo[3.2.1]oct-2-enyl nonaflates

Tetrahedron

Volumn 60, Issue 35, 2004, Pages 7721-7729

  Lyapkalo, Ilya M ^a,b   Högermeier, Jens ^a   Reissig, Hans Ulrich ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

^b INSTITUTE OF CHEMICAL AND ENGINEERING SCIENCES   (Singapore)

Author keywords

Alkenyl sulfonates; Diels Alder reaction; Nonaflates; Palladium catalysis; Tropinone

Indexed keywords

(8 ETHOXYCARBONYL 8 AZABICYCLO[3.2.1]OCT 2 EN 3 YL)NONAFLATE; (8 METHOXYCARBONYL 8 AZABICYCLO[3.2.1]OCTA 2,6 DIEN 3 YL)NONAFLATE; 15 ETHYL 8 METHYL 4,6 DIOXO 5 PHENYL 5,15 DIAZATETRACYCLO[10.2.1.0 2,10 .0 3,7 ]PENTADEC 9 ENE 8,15 DICARBOXYLATE; 8 METHYL 8 AZABICYCLO[3.2.1]OCT 2 EN 3 YLNONAFLATE; ACETYLENE DERIVATIVE; ACRYLIC ACID; ACRYLIC ACID METHYL ESTER; ACRYLONITRILE; ALKADIENE; CARBOXYLIC ACID DERIVATIVE; ETHER DERIVATIVE; ETHYL 3 (2 CYANOETHYL) 8 AZABICYCLO[3.2.1]OCT 2 ENE 8 CARBOXYLATE; ETHYL 3 (2 PHENYLETHENYL) 8 AZABICYCLO[3.2.1]OCT 2 ENE 8 CARBOXYLATE; ETHYL 3 [2 (PHENYLSULFONYL)ETHENYL] 8 AZABICYCLO[3.2.1]OCT 2 ENE 8 CARBOXYLATE; FLUORIDE; KETONE; MALEIMIDE DERIVATIVE; METHYL 3 (8 ETHOXYCARBONYL 8 AZABICYCLO[3.2.1]OCT 2 EN 3 YL)PROPENOATE; N PHENYLMALEIMIDE; NONAFLUOROBUTANESULFONYL FLUORIDE; OCTANE; PALLADIUM; PHENYLACETYLENE; PHENYLVINYLSULFONE; PROPYLENE; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; DIELS ALDER REACTION; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH TEMPERATURE PROCEDURES; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; SONOGASHIRA REACTION;

BETULACEAE;

EID: 3843098415     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.06.036     Document Type: Article

References (37)

1. Review: Singh S. Chem. Rev. 100:2000;925-1024
2. Selected recent examples of syntheses of cocaine analogues and related derivatives: Höpping A., George C., Flippen-Anderson J., Kozikowski A.P. Tetrahedron Lett. 41:2000;7427-7432
3. Deng S.X., Huang D.W., Landry D.W. Tetrahedron Lett. 42:2001;6259-6261
4. Isomura S., Hoffman T.Z., Wirsching P., Janda K.D. J. Am. Chem. Soc. 124:2002;3661-3668
5. Davies H.M.L., Ren P., Kong N.X., Sexton T., Childers S.R. Bioorg. Med. Chem. Lett. 12:2002;845-847
6. Gündisch D., Kämpchen T., Schwarz S., Seitz G., Siegl J., Wegge T. Bioorg. Med. Chem. 10:2002;1-9
7. Zou M., Agoston G.E., Belov Y., Kopajtic T., Katz J.L., Newman A. Bioorg. Med. Chem. Lett. 12:2002;1249-1252
8. Bradley A.L., Izenwasser S., Wade D., Klein-Stevens D., Zhu N., Trudell M.L. Bioorg. Med. Chem. Lett. 12:2002;2387-2390
9. Gong L., Hogg J.H., Collier J., Wilhelm R.S., Soderberg C. Bioorg. Med. Chem. Lett. 13:2003;3597-3600
10. Nussbaumer P., Geyl D., Horvath A., Lehr P., Wolff B., Billich A. Bioorg. Med. Chem. Lett. 13:2003;3673-3677
11. Cramer N., Laschat S., Baro A., Frey W. Synlett. 2003;2175-2177
12. For palladium-catalyzed reactions of alkenyl triflates with 8-azabicyclo[3.2.1]oct-2-ene skeleton see: Wegge T., Schwarz S., Seitz G. Pharmazie. 55:2000;779-780
13. Lu Z., Tata J.R., Cheng K., Wei L., Chan W.W.-S., Butler B., Schleim K.D., Jacks T.M., Hickey G., Patchett A.A. Bioorg. Med. Chem. Lett. 13:2003;1817-1820
14. Webel M., Reissig H.-U. Synlett. 1997;1141-1142
15. Lyapkalo I.M., Webel M., Reissig H.-U. Eur. J. Org. Chem. 2001;4189-4194
16. Lyapkalo I.M., Webel M., Reissig H.-U. Eur. J. Org. Chem. 2002;1015-1025
17. Lyapkalo I.M., Webel M., Reissig H.-U. Eur. J. Org. Chem. 2002;3646-3658
18. Lyapkalo I.M., Webel M., Reissig H.-U. Synlett. 2001;1293-1295
19. For contributions of other research groups concerning palladium-catalyzed reactions of alkenyl or aryl nonaflates: Bräse S., de Meijere A. Angew. Chem. 107:1995;2741-2743
20. Bräse S., de Meijere A. Angew. Chem., Int. Ed. Engl. 34:1995;2545
21. Voigt K., von Zezschwitz P., Rosauer K., Lansky A., Adams A., Reiser O., de Meijere A. Eur. J. Org. Chem. 1998;1521-1534
22. Rottlaender M., Knochel P. J. Org. Chem. 63:1998;203-208
23. Bräse S. Synlett. 1999;1654-1656
24. For a review on perfluoroalkyl sulfonates in palladium-catalyzed reactions see: Ritter K. Synthesis. 1993;735-762
25. Limat D., Schlosser M. Tetrahedron. 51:1995;5799-5806
26. Armstrong A., Hayter B.R., Moss W.O., Reeves J.R., Wailes J.S. Tetrahedron: Asymmetry. 11:2000;2057-2062
27. Sonogashira K., Tohda Y., Hagihara N. Tetrahedron Lett. 16:1975;4467-4470
28. 2,7]dodecane skeleton are apparently almost unknown. A CAS substructure search offered only one hit of a commercially available compound containing this skeleton, however, no reference was given
29. Högermeier, J.; Reissig, H.-U.; Brüdgam, I.; Harte, H. Adv. Synth. Catal. 2004, in press and Högermeier, J.; Reissig, H.-U. Unpublished results.
30. Högermeier, J.; Reissig, H.-U.; Brüdgam, I.; Harte, H. Adv. Synth. Catal. 2004, in press and Högermeier, J.; Reissig, H.-U. Unpublished results.
31. Mann J., de Almeida Barbosa L.-C. J. Chem. Soc., Perkin Trans. 1. 1992;787-790
32. Selected reviews: Heck R.F. Org. React. (N.Y.). 27:1982;345-390
33. de Meijere A., Meyer F.E. Angew. Chem. 106:1994;2473-2506
34. de Meijere A., Meyer F.E. Angew. Chem., Int. Ed. Engl. 33:1994;2379-2411
35. For an acid induced retro-Mannich reaction of N-protected tropinones leading to similar products see: Cramer N., Juretschke J., Laschat S., Baro A., Frey W. Eur. J. Org. Chem. 2004;1397-1400
36. Review: Burke M.D., Schreiber S.L. Angew. Chem. 116:2004;48-60
37. Burke M.D., Schreiber S.L. Angew. Chem., Int. Ed. 43:2004;46-58