Magnesium bromide promoted barbier-type intramolecular cyclization of halo-substituted acetals, ketals, and orthoesters

Tetrahedron Letters

Volumn 40, Issue 49, 1999, Pages 8647-8650

  Huang, Jui Wen ^a   Chen, Chiar Dy ^a   Leung, Man kit ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; ALKANONE; CYCLOALKANOL DERIVATIVE; ESTER DERIVATIVE; KETONE DERIVATIVE; MAGNESIUM DERIVATIVE; REAGENT;

ARTICLE; CATALYST; CYCLIZATION; MOLECULAR INTERACTION; REACTION ANALYSIS;

EID: 0033521156     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01813-4     Document Type: Article

References (30)

1. (a) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2 nd. Wiley: New York, 1990.
2. (b) Kocienski, P. J. Protective Groups; Thieme: New York, 1994.
3. (a) Feugeas, C.; Bull. Soc. Chim. Fr. 1963, 2568.
4. (b) Blomberg, C.; Hartog, F. A. Synthesis 1977, 18.
5. For examples, see (a) van der Gen, A.; Wiehaupt, K.; Swoboda, J. J.; Dunathan, H. C.; Johnson, W. S. J. Am. Chem. Soc. 1973, 95, 2656.
6. (b) Johnson, W. S.; Wiehaup, K.; Brady, S. F.; Olsen, G. L. J. Am. Chem. Soc. 1974, 96, 3979.
7. (c) Poller, R. C.; Abbas, S. Z. J. Chem. Soc., Dalton Trans. 1974, 1769.
8. (d) Casals, P. F.; Ferard, J. Tetrahedron Lett. 1974, 2483.
9. (e) Forbes, C. P.; Wenteler, G. L.; Wiechers, A. J. Chem. Soc., Perkin Trans. 1 1977, 2353.
10. (f) Sworin, M.; Neumann, W. L. Tetrahedron Lett. 1987, 3217.
11. For a review, see: Bickelhaupt, F. Angew. Chem., Int. Ed. Engl. 1987, 26, 990.
12. For references of Lewis-acid assisted mechanisms, see (a) Mukaiyama, T.; Murakami M. Synthesis 1987, 1043.
13. (b) Ishihara K.; Mori, A.; Yamamoto, H. Tetrahedron 1990, 46, 4595.
14. (c) Denmark, S. E.; Almstead, N. G. J. Org. Chem. 1991, 56, 6458; J. Am. Chem. Soc. 1991, 113, 8089.
15. (c) Denmark, S. E.; Almstead, N. G. J. Org. Chem. 1991, 56, 6458; J. Am. Chem. Soc. 1991, 113, 8089.
16. (d) Ishihara K.; Hanaki, N; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10695.
17. (e) Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 477.
18. (f) Hunter, R.; Bartels, B. J. Org. Chem. 1993, 58, 6756.
19. (g) Fujioka, H.; Kitagawa, H.; Matsunaga, N.; Nagatomi, Y.; Kita, Y. Tetrahedron Lett. 1996, 2245.
20. (h) Sammakia, T.; Smith, R. J. Am. Chem. Soc. 1992, 114, 10998; J. Org. Chem. 1992, 57, 2997.
21. (h)Sammakia, T.; Smith, R. J. Am. Chem. Soc. 1992, 114, 10998; J. Org. Chem. 1992, 57, 2997.
22. (i) Mori, A.; Fujiwara, J.; Maruoka, K.; Yamamoto, H. J. Organomet. Chem. 1985, 285, 83.
23. (j) Mori, I.; Ishihara, K.; Flippin, L. A.; Nozaki, K.; Yamamoto, H.; Barlett, P.; Heathcock, C. H. J. Org. Chem. 1990, 55, 6107.
24. (k) Mallory, R.; Rovinski, S.; Kohen, F.; Scheer, I. J. Org. Chem. 1967, 32, 1417.
25. (l) Ishikawa, H.; Mukaiyama, T.; Ikeda, S. Bull. Chem. Soc. Jpn. 1981, 54, 776.
26. (m) Westera, G.; Blomberg, C.; Bickelhaupt, F. J. Organomet. Chem. 1978, 144, 285.
27. (n) Westera, G.; Blomberg, C.; Bickelhaupt, F. J. Organomet. Chem. 1978, 144, 285, 290.
28. (o) Yuan, T. M.; Yeh, S. M.; Hsieh, Y. T.; Yuan, T. M. J. Org. Chem. 1994, 59, 8192.
29. Mendolini, L. Adv. Phys. Org. Chem. 1986, 22, 1.
30. Cowan, D. O.; Mosher, H. S. J. Org. Chem. 1962, 27, 1.