Introduction of bromine and chlorine substituents in medium ring ethers and lactones

Abstract

A convenient preparation of α-halo enamines using oxalyl halides is described together with applications of these reagents in the halogenation of β-hydroxy cyclic ethers and lactones.

References

1. C. J. Moody and M. J. Davies, in Studies in Natural Product Chemistry, ed. Atta-ur-Rahman, Elsevier, 1992, vol. 10, pp. 201–239; M. C. Elliott, Contemp. Org. Synth., 1994, 1, 457; G. Rousseau, Tetrahedron, 1995, 51, 2777; K. C. Nicolaou, Angew. Chem., Int. Ed. Engl., 1996, 35, 589.
2. R. W. Carling, J. S. Clark and A. B. Holmes, J. Chem. Soc., Perkin Trans. 1, 1992, 83; R. W. Carling, J. S. Clark, A. B. Holmes and D. Sartor, J. Chem. Soc., Perkin Trans. 1, 1992, 95.
3. J. S. Clark and A. B. Holmes, Tetrahedron Lett., 1988, 29, 4333.
4. N. R. Curtis, A. B. Holmes and M. G. Looney, Tetrahedron Lett., 1992, 33, 671.
5. T. Masamune, H. Murase, H. Matsue and A. Murai, Bull. Chem. Soc. Jpn., 1979, 52, 135; K. Tsushima and A. Murai, Tetrahedron Lett., 1992, 33, 4345; M. Bratz, W. H. Bullock, L. E. Overman and T. Takemoto, J. Am. Chem. Soc., 1995, 117, 5958.
6. A. P. Kozikowski and J. M. Lee, Tetrahedron Lett., 1988, 29, 3053; J. Org. Chem., 1990, 55, 863.
7. L.-X. Gao and A. Murai, Tetrahedron Lett., 1992, 33, 4349.
8. E. Lee, C. M. Park and J. S. Yun, J. Am. Chem. Soc., 1995, 117, 8017.
9. A. Streitwieser, Solvolytic Displacement Reactions, McGraw-Hill, New York, 1962, p. 113.
10. K. Fujiwara, M. Tsunashima, D. Awakura and A. Murai, Tetrahedron Lett., 1995, 36, 8263.
11. A. J. Speziale and R. C. Freeman, J. Am. Chem. Soc., 1959, 81, 903.
12. A. J. Speziale and R. C. Freeman, J. Am. Chem. Soc., 1960, 82, 909.
13. A. Colens, M. Demuylder, B. Techy and L. Ghosez, Nouv. J. Chem., 1977, 1, 369.
14. B. Haveaux, A. Dekoker, M. Rens, A. R. Sidani, J. Toye and L. Ghosez, Org. Synth., 1980, 59, 26.
15. A. Devos, J. Remoin, A. M. Fisque-Hesbian, A. Colens and L. Ghosez, J. Chem. Soc., Chem. Commun., 1979, 1180.
16. A. B. Holmes, C. L. D. Jennings-White and D. A. Kendrick, J. Chem. Soc., Chem. Commun., 1983, 415.
17. F. Munyemana, A.-M. Frisque-Hesbain, A. Devos and L. Ghosez, Tetrahedron Lett., 1989, 30, 3077.
18. N. P. van Vliet(N. V. Organon), ZA 7 200 618 (Chem. Abstr., 1973, 78, 136532).
19. M. S. Congreve, A. B. Holmes, A. B. Hughes and M. G. Looney, J. Am. Chem. Soc., 1993, 115, 5815.
20. J. W. Burton, J. S. Clark, S. Derrer, T. C. Stork, J. G. Bendall and A. B. Holmes, submitted for publication (cf.J. Am. Chem. Soc., 1996, 118, 6806).
21. A. Wagner, M.-P. Heitz and C. Miokowski, Tetrahedron Lett., 1989, 30, 557.
22. G. Lange and C. Gottardo, Magn. Res. Chem., 1990, 28, 659.