Efficient and Catalytic Conversion of Epoxides to 1,3-Dioxolanes with TiO(TFA)₂ or TiCl₃(OTf)

Abstract

TiO(TFA)₂ or TiCl₃(OTf) catalyses the efficient reaction of epoxides with acetone to give the corresponding 1,3-dioxolanes in excellent yields. The reaction of chiral styrene oxide was found to be highly stereospecific.

References

1. T. H. Green and P. G. M. Wuts, Protective Groups in Organic Synthesis, 2nd edn., Wiley, New York, 1991, pp. 188–195.
2. F. A. J. Meskens, Synthesis, 1981, 501.
3. R. P. Hanzlik and M. Leinwetter, J. Org. Chem., 1978, 43, 438.
4. (a) L. W. Zatorski and P. T. Wierzchowski, Catal. Lett., 1991, 10, 211; (b) H. Steinbrink, Chemische Werke Huls AG, Ger. Pat. (DOS), 1086241, 1959(Chem. Abstr., 1962, 56, 5969); (c) A. A. Gevorkyan, P. I. Kazaryan, O. V. Avakyan and R. A. Vardanyan, Khim. Geterotsikl. Soedin, 1991, 1, 33 (Chem. Abstr., 1991, 115, 8633x).
5. B. Rickborn and R. M. Gerkin, J. Am. Chem. Soc., 1971, 93, 1693.
6. P. F. Hudrlik, R. N. Misra, G. P. Withers, H. M. Hudrlik, R. J. Rona and J. P. Arcoleo, Tetrahedron Lett., 1976, 1453.
7. J. Kagan, B. E. Firth, N. Y. Shih and C. Boyajian, J. Org. Chem., 1977, 42, 343.
8. D. J. Harvey, Res. Commun. Chem. Pathol. Pharmacol., 1972, 4, 247.
9. (a) D. S. Torok, J. J. Figueroa and W. J. Scott, J. Org. Chem., 1993, 58, 7274; (b) T. Nagata, T. Takai, T. Yamada, K. Imagawa and T. Mukaiyama, Bull. Chem. Soc. Jpn., 1994, 67, 2614.
10. P. Sartori, Angew Chem., 1964, 76, 376.
11. (a) R. Noftle and G. H. Cady, Inorg. Chem., 1966, 5, 2182; (b) H. Moulay el Mustapha and J. L. Pascal, J. Fluorine Chem., 1991, 55, 63.
12. A. L. Shabanov, M. M. Movsumzade, N. G. Kerimova, A. S. Kyazimov and V. S. Mamedzade, Uch. Zap. Azerb. Inst. Nefti Khim., Ser. 9, 1971, 8, 78.