Enzyme-mediated synthesis of (R)- and (S )-α-ionone

Abstract

Diastereoisomeric enrichment through fractional crystallisation of 4-nitrobenzoate derivatives of α-ionol, and enantioselective enzyme-mediated reactions of α-ionol and α-ionol acetate, were usefully combined to optimise two different procedures to enantiopure (S )- and (R)-ionone.

References

1. F. Tiemann and F. Krueger, Ber. Dtsch. Chem. Ges., 1893, 26, 2675.
2. F. Tiemann, Ber. Dtsch. Chem. Ges., 1898, 31, 808.
3. G. Uhde and G. Ohloff, Helv. Chim. Acta, 1972, 55, 2621.
4. R. Buchecker, R. Egli, H. Regel-Wild, C. Tscharner, C. H. Eugster, G. Uhde and G. Ohloff, Helv. Chim. Acta, 1973, 56, 2548.
5. E. H. Polak, A. M. Forobon, C. Tilquin and P. H. Punter, Behav. Brain Res., 1989, 31, 199.
6. C. Fehr and O. Guntern, Helv. Chim. Acta, 1992, 75, 1023.
7. P. Werkhoff, W. Bretschneider, M. Guentert, R. Hopp and H. Surburg, Flavor Science and Technology, ed. Y. Bessiere and A. F. Thomas, J. Wiley & Sons, New York, 1990, p. 33.
8. H. Sobotka, E. Bloch, H. Cahnmann, E. Feldbau and E. Rosen, J. Am. Chem. Soc., 1943, 65, 2061; Y. R. Naves, Helv. Chim. Acta, 1947, 30, 769.
9. R. B. Woodward, T. P. Kohman and G. C. Harris, J. Am. Chem. Soc., 1941, 63, 120.
10. C. Fehr and J. Galindo, J. Am. Chem. Soc., 1988, 110, 6909.
11. H. Pfander and P. A. Semadeni, Aust. J. Chem., 1995, 48, 145.
12. E. Brenna, N. Caraccia, C. Fuganti, D. Fuganti and P. Grasselli, Tetrahedron: Asymmetry, 1997, 8, 3801.
13. A. J. Aasen, B. Kimland and C. R. Enzell, Acta Chem. Scand., Ser. B, 1973, 27, 2107.
14. L. Palfray, S. Sabetay and J. Kandel, C. R. Hebd. Seances Acad. Sci., 1936, 203, 1376.
15. O. Mitsunobu, Synthesis, 1981, 1.
16. J. Attenburrow, A. F. B. Cameron, J. H. Chapman, R. M. Evans, B. A. Hems, A. B. A. Jansen and T. Walker, J. Chem. Soc., 1952, 1094.
17. C. S. Chen, Y. Fujimoto, G. Girdaukas and C. J. Sih, J. Am. Chem. Soc., 1982, 104, 7294.