Highly chemo- and regioselective rearrangement of α,β-epoxy ketones to 1,3-dicarbonyl compounds in 5 mol dm^–3 lithium perchlorate–diethyl ether medium

Abstract

Epoxides from α,β-unsaturated ketones undergo highly chemo- and regioselective rearrangement to 1,3-dicarbonyl compounds in 5 mol dm^–3 lithium perchlorate–diethyl ether medium by a 1,2-migration of the carbonyl group at ambient conditions.

References

1. B. Rickborn, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon Press, New York, 1991, vol. 3, pp. 733–775.
2. R. Sudha, K. Malol Narasimhan, V. Geeth Saraswathy and S. Sankararaman, J. Org. Chem., 1996, 61, 1877.
3. H. O. House and R. L. Wasson, J. Am. Chem. Soc., 1956, 78, 4394; M. Suzuki, A. Watanabe and R. Noyori, J. Am. Chem. Soc, 1980, 102, 2095; T. Bharat Rao and J. Madhusudana Rao, Synth. Commun., 1993, 23, 1527; R. D. Bach, M. W. Tubergen and R. C. Klix, Tetrahedron Lett., 1986, 27, 3565; R. D. Bach and R. C. Klix, J. Org. Chem., 1985, 50, 5438; J. R. Williams, G. M. Sarkisian, J. Quigley, A. Hasiuk and R. Vander Venner, J. Org. Chem., 1974, 39, 1028.
4. H. O. House and G. D. Ryerson, J. Am. Chem. Soc., 1961, 83, 979.
5. R. D. Bach and R. C. Klix, Tetrahedron Lett., 1985, 26, 985; R. D. Bach and J. M. Domagala, J. Org. Chem., 1984, 49, 4181.
6. G. Springer, C. Elam, A. Edwards, C. Bowe, D. Boyles, J. Bartmess, M. Chandler, K. West, J. Williams, J. Green, R. M. Pagni and G. W. Kabalka, J. Org. Chem., 1999, 64, 2202; R. M. Pagni, G. W. Kabalka, S. Bains, M. Pleasco, J. Wilson and J. Bartmess, J. Org. Chem., 1993, 58, 3130.
7. V. Geetha Saraswathy and S. Sankararaman, J. Org. Chem., 1994, 59, 4665; 1995, 60, 5024; J. Chem. Soc., Perkin Trans. 2, 1996, 29.
8. P. A. Zoretic, R. J. Chambers, G. D. Marbury and A. A. Riebiro, J. Org. Chem., 1985, 50, 2981.
9. G. Sathyamoorthi, K. Thangaraj, P. C. Srinivasan and S. Swaminathan, Tetrahedron, 1990, 46, 3559.
10. S. Li, K. Lundquist and R. Stomberg, Acta Chem. Scand., 1993, 47, 867; P. S. Kulkarni, S. V. Kamath, K. S. Kamath and N. Sheshgiri, Org. Mass Spectrom., 1984, 19, 482.
11. I. Hideharu and H. Yoshio, Chem. Lett., 1978, 1007.
12. T. Inukai and R. Yoshizawa, J. Org. Chem., 1967, 32, 404.
13. H. O. House and R. L. Wasson, J. Am. Chem. Soc., 1957, 79, 1488.
14. F. Kunisch, K. Hobert and P. Welzel, Tetrahedron Lett., 1985, 26, 6039.
15. C. M. Cimarusti and J. Wolinsky, J. Org. Chem., 1966, 31, 4118.
16. R. C. Klix and R. D. Bach, J. Org. Chem., 1987, 52, 580.