An efficient enantioselective synthesis of (+)-(R,Z)-5-muscenone and (-)-(R)-muscone - An example of a kinetic resolution and enantioconvergent transformation

European Journal of Organic Chemistry

Volumn , Issue 9, 2004, Pages 1953-1957

  Fehr, Charles ^a   Galindo, José ^a   Etter, Olivier ^a  

^a Email:   (Switzerland)

Author keywords

Enantioconvergence; Kinetic resolution; Macrocycles; Odorants; Reduction

Indexed keywords

MUSCONE; MUSK; PALLADIUM;

ARTICLE; CATALYSIS; CYCLIZATION; ENANTIOSELECTIVITY; KINETICS; SYNTHESIS;

EID: 4043135580     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400037     Document Type: Article

References (28)

1. E. Demole, C. Mahaim, P.-A. Blanc, EP 584477 to Firmenich (prior. 30. July 1992); Chem. Abstr. 1994, 120, 253101.
2. [2a] P. Scafato, S. Labano, G. Cunsolo, C. Rosini, Tetrahedron: Asymmetry 2003, 14, 3873.
3. [2b] P. K. Fraser, S. Woodward, Chem. Eur. J. 2003, 9, 776.
4. [2c] S. Fujimoto, K. Yoshikawa, M. Itoh, T. Kitahara, Biosci. Biotechnol. Biochem. 2002, 66, 1389.
5. [2d] T. Yamamoto, M. Ogura, T. Kanisawa, Tetrahedron 2002, 58, 9209.
6. [2e] Y. H. Choi, J. Y. Choi, Y. Yang, Y. H. Kim, Tetrahedron: Asymmetry 2002, 13, 801.
7. [2f] Y. Matsumura, H. Fukawa, A. Endo, JP 2002-335991, 2002; Chem. Abstr. 2002, 137, 383885.
8. [2g] G. Kim, M. S. Park, J. H. Yoo, S. Y. Lee, KR 2000049980, 2000; Chem. Abstr. 2002, 137, 124944.
9. [2h] A. Alexakis, C. Benhaïm, X. Fournioux, A. van den Heuvel, J.-M. Levêque, S. March, S. Rosset, Synlett 1999, 1811 and references cited therein.
10. [2c]
11. [3b] For the synthesis of a mixture of isomers of (S)-1 and (S)-2 (+ positional isomers?): D.-S. Wang, D.-Q. Wang, C.-H. Zhou, Huaxue Xuebao 1995, 53, 909.
12. [3c] See also: D. Wang, C. Zhou, D. Wang, Chin. Chem. Lett. 1992, 3, 235.
13. -3 μg/L air.
14. E. J. Corey, C. J. Helal, Angew. Chem. Int. Ed. 1998, 37, 1986.
15. J. Schreiber, D. Felix, A. Eschenmoser, M. Winter, F. Gautschi, K. H. Schulte-Elte, E. Sundt, G. Ohloff, J. Kalvoda, H. Kaufmann, P. Wieland, G. Anner, Helv. Chim. Acta 1967, 50, 2101.
16. [7a] G. Ohloff, J. Becker, K. H. Schulte-Elte, Helv. Chim. Acta 1967, 50, 705.
17. [7b] For a review of the synthesis of macrocyclic musks, see: A. S. Williams, Synthesis 1999, 1707.
18. P. Dorizon, C. Martin, J.-C. Daran, J.-C. Fiaud, H. B. Kagan, Tetrahedron: Asymmetry 2001, 12, 2625.
19. The same tendency was noticed with stoichiometric amounts of the oxazaborolidine 6 [(-)-7: 7% conv.: 75% ee; 20% conv.: 81% ee).
20. In general, the formed alkoxyboranes are suspected to be responsible for decreased enantioselectivities. For the beneficial effect of added 2-propanol (in certain cases), thought to be due to a more rapid transformation of the oxazaborolidine-complexed alkoxyborane into the initial catalytic species, see: A. W. Douglas, D. M. Tschaen, R. A. Reamer, Y.-J. Shi, Tetrahedron: Asymmetry 1996, 7, 1303.
21. [11a] J. M. Goodman, A.-K. Köhler, S. C. M. Alderton, Tetrahedron Lett. 1999, 40, 8715.
22. [11b] H. B. Kagan, J. C. Fiaud, Top. Stereochem. 1988, 18, 249.
23. I. Kovarova, L. Streinz, Synth. Commun. 1993, 23, 2397.
24. Whereas (R)-1 and (R)-2 represent strong musk odorants, (S)-1 and (S)-2 are only weakly musky. (R)-10 is weakly musky and (S)-10 is almost odorless.
25. K. Utimoto, Pure Appl. Chem. 1983, 55, 1845.
26. The isomeric enol ether having the double bond in the macrocycle was not detected.
27. Other catalysts tested (e.g. Pd/C/MeOH) gave partial racemization. For a more detailed study, see: C. Fehr, J. Galindo, I. Farris, A. Cuenca, Helv. Chim. Acta., in press.
28. For the preparation of 6, see: D. J. Mathre, T. K. Jones, L. C. Xavier, T. J. Blacklock, R. A. Reamer, J. J. Mohan, E. T. Turner Jones, K. Hoogsteen, M. W. Baum, E. J. J. Grabowski, J. Org. Chem. 1991, 56, 751.