(-)-(9R,10S)-10-Acetyl-9,10-dimethylbicyclo[6.4.0]dodec-1(8)-ene: Optical Resolution, Catalyst Systems, Derivatives and Olfactory Properties

Synthesis

Volumn , Issue 3, 2004, Pages 381-388

  Kraft, Philip ^a   Gallo, Sofia ^a  

^a GIVAUDAN SCHWEIZ AG   (Switzerland)

Author keywords

Catalysis; Cycloadditions; Enantiomeric resolution; Odorants; Polycycles

Indexed keywords

ADDITION REACTIONS; CATALYSTS; DERIVATIVES; ISOMERS; MOLECULAR STRUCTURE; ODORS; OPTICAL RESOLVING POWER; SYNTHESIS (CHEMICAL);

ENANTIOMERS; ODORANTS;

AROMATIC COMPOUNDS;

10 ACETYL 9,10 DIMETHYLBICYCLO[6.4.0]DODEC 1(8) ENE; 2 METHYLTRICYCLO[7.6.0.0 3,7 ]PENTADEC 1(9) EN 4 ONE; 2,3 DIMETHYLTRICYCLO[7.6.0.0 3,7 ]PENTADEC 1(9) EN 4 ONE; ALKENE DERIVATIVE; DECANE; PLATINUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CYCLOADDITION; DIASTEREOISOMER; ENANTIOMER; ODOR; SEPARATION TECHNIQUE;

EID: 1442359955     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-815943     Document Type: Article

References (35)

1. Gallo, S. Diploma Thesis; Eidgenössische Technische Hochschule Zürich, Dept. XAf: Switzerland, 2003.
2. (a) Fráter, G.; Bajgrowicz, J. A.; Kraft, P. Tetrahedron 1998, 54, 7633.
3. (b) Kraft, P.; Bajgrowicz, J. A.; Denis, C.; Fráter, G. Angew. Chem. Int. Ed. 2000, 39, 2980; Angew. Chem. 2000, 112, 3106.
4. (b) Kraft, P.; Bajgrowicz, J. A.; Denis, C.; Fráter, G. Angew. Chem. Int. Ed. 2000, 39, 2980; Angew. Chem. 2000, 112, 3106.
5. Nussbaumer, C.; Fráter, G.; Kraft, P. Helv. Chim. Acta 1999, 82, 1016.
6. Kraft, P. Synthesis 1999, 695.
7. Ruder, S. M.; Ronald, R. C. Tetrahedron Lett. 1984, 25, 5501.
8. Doering, W. V. E.; Schreiber, K. C. J. Am. Chem. Soc. 1955, 77, 514.
9. Fitjer, L.; Quabeck, U. Synth. Commun. 1985, 15, 855.
10. (a) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720.
11. (b) Wender, P. A.; Baryza, J. L.; Brenner, S. E.; Clarke, M. O.; Gamber, G. G.; Horan, J. C.; Jessop, T. C.; Kan, C.; Pattabiraman, K.; Williams, T. J. Pure Appl. Chem. 2003, 75, 143.
12. (c) Wender, P. A.; Williams, T. J. Angew. Chem. Int. Ed. 2002, 41, 4550; Angew. Chem. 2002, 114, 4732.
13. (c) Wender, P. A.; Williams, T. J. Angew. Chem. Int. Ed. 2002, 41, 4550; Angew. Chem. 2002, 114, 4732.
14. (a) Job, A.; Janeck, C. F.; Bettray, W.; Peters, R.; Enders, D. Tetrahedron 2002, 58, 2253.
15. (b) Djuric, S. W.; Docter, S. H.; Yu, S. S.; Spangler, D.; Tsai, B.-S.; Anglin, C. P.; Gaginella, T. S.; Kachur, J. F.; Keith, R. H.; Masiasz, T. J.; Villani-Price, D.; Rao, T. S.; Walsh, R. E.; Widomski, D. L.; Fretland, D. J. Bioorg. Med. Chem. Lett. 1994, 4, 811.
16. (c) Domínguez, D.; Ardecky, R. J.; Cava, M. P. J. Am. Chem. Soc. 1983, 105, 1608.
17. (a) Gerlach, H. Helv. Chim. Acta 1968, 51, 1587.
18. (b) Gerlach, H.; Müller, W. Helv. Chim. Acta 1972, 55, 2277.
19. (c) Helmchen, G.; Staiger, G. Angew. Chem. Int. Ed. Engl. 1977, 16, 116; Angew. Chem. 1977, 89, 119.
20. (c) Helmchen, G.; Staiger, G. Angew. Chem. Int. Ed. Engl. 1977, 16, 116; Angew. Chem. 1977, 89, 119.
21. (d) Oppolzer, W.; Chapuis, C.; Dupuis, D.; Guo, M. Helv. Chim. Acta 1985, 68, 2100.
22. (e) Tochtermann, W.; Mattauch, A.-K.; Kasch, M.; Peters, E.-M.; Peters, K.; von Schnering, H. G. Liebigs Ann. 1996, 317.
23. Boaz, N. W.; Debenham, S. D.; Mackenzie, E. B.; Large, S. E. Org. Lett. 2002, 4, 2421.
24. (a) Periana, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1984, 106, 7272.
25. (b) Periana, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1986, 108, 7346.
26. (c) Stang, P. J.; Song, L.; Lu, Q.; Halton, B. Organometallics 1990, 9, 2149.
27. (a) Miyashita, A.; Takahashi, M.; Takaya, H. J. Am. Chem. Soc. 1981, 103, 6257.
28. (b) Burton, J. T.; Puddephatt, R. J. Organometallics 1983, 2, 1487.
29. (c) Wilker, C. N.; Hoffmann, R. J. Am. Chem. Soc. 1983, 105, 5285.
30. (d) Burton, J. T.; Puddephatt, R. J. Organometallics 1986, 5, 1312.
31. (e) Parsons, E. J.; Jennings, P. W. J. Am. Chem. Soc. 1987, 109, 3973.
32. (f) Neilsen, W. D.;Larsen, R. D.; Jennings, P. W. J. Am. Chem. Soc. 1988, 110, 3307.
33. (g) Parsons, E. J.; Jennings, P. W. Organometallics 1988, 7, 1435.
34. (h) Neilsen, W. D.; Larsen, R. D.; Jennings, P. W. J. Am. Chem. Soc. 1988, 110, 8657.
35. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-217321, CCDC-218099, and CCDC-219739. 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; E-mail: deposit@ccdc.cam.ac.uk].