Page 84 - Catalysts for Fine Chemical Synthesis Vol 1 - Robert & Poignant

epoxidation of a, b-unsaturated carbonyl compounds 69

. All of the reagents required for the asymmetric epoxidation are commer-
cially available.
. Both enantiomers of a, b-epoxy ketones can be synthesized essentially at the
same cost since both (R)- and (S)-BINOLs are sold at almost the same price.
. It may not be necessary to employ an optically pure chiral ligand (BINOL)
for the preparation of the catalyst because a high degree of asymmetric
amplification can be expected.

REFERENCES

1. Bentley, P.A., Bergeron, S., Cappi, M.W., Hibbs, D.E., Hursthouse, M.B., Nugent,
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2. Daly, W.H., Poche Â, D. Tetrahedron Lett., 1988, 29, 5859.
3. Itsuno, S., Sakakura, M., Ito, K. J. Org. Chem., 1990, 55, 6047.
4. Bentley, P.A., Kroutil, W., Littlechild, J.A., Roberts, S.M. Chirality, 1997, 9, 198.
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Thornton, S.R., Todd, C.J., Tu Èter, M. J. Chem. Soc., Chem. Commun., 1996, 845.
6. Roberts, S.M. Preparative Biotransformations, Wiley, Chichester 1997.
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9. Kher, S.M., Kulkarni, G.H. Synth. Commun., 1990, 20, 2573.
10. Pure CMHP was obtained by the method in Purification of Laboratory Chemicals,
4th ed.; Perrin, D.D., Armarego, W.L., Eds; Butterworth-Heinemann: Oxford, pp.
154, 1996.
11. Daikai, K., Kamaura, M., and Inanaga, J., Tetrahedron Lett., 1998, 39, 7321.
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