Selective isomerization of aryl substituted epoxides to aldehydes via iron Lewis acid catalysis

Tetrahedron Letters

Volumn 39, Issue 18, 1998, Pages 2681-2684

  Picione, John ^a   Mahmood, Syed J ^a   Gill, Andy ^a   Hilliard, Marion ^a   Hossain, M Mahmun ^a  

^a UNIVERSITY OF WISCONSIN MILWAUKEE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ALDEHYDE; EPOXIDE; IRON;

ARTICLE; CATALYSIS; ISOMERISM; REACTION ANALYSIS;

EID: 0032580345     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00371-2     Document Type: Article

References (29)

1. 1. (a) House, H. O. J. Am. Chem. Soc. 1955, 77, 3070; 5083; Org. Synth. Coll. Vol. IV, 1963, 375.
2. 1. (a) House, H. O. J. Am. Chem. Soc. 1955, 77, 3070; 5083; Org. Synth. Coll. Vol. IV, 1963, 375.
3. (b) Stork, G.; Colvin, E. J. Am. Chem. Soc. 1971, 93, 2080.
4. (c) Maruoka, K.; Nagahara, S.; Ooi, T.; Yamamoto, H. Tetrahedron Lett. 1989, 30, 5607.
5. (d) Yanagisawa, A.; Yasue, K. Yamamoto, H. J. Chem. Soc. Chem. Commun. 1994, 2103.
6. 2. (a) Crandall, J. K.; Apparu, M. Org. React. 1983, 29, 345.
7. (b) Smith, J. G. Synthesis 1984, 629.
8. (c) Larock, R. C. Comprehensive Organic Transformations. VCH. New York, 1989, p 628.
9. (d) Rickborn, B. in Comprehensive Organic Synthesis, ed. Trost, B. M.; Fleming, I; Pattenden, G. Pergamon, Oxford, 1991, vol. 3, p.733.
10. 3. (a) Eisenmann, J. L. J Org. Chem. 1962, 27, 2706.
11. (b) Milstein, D.; Buchman, O.; Blum, J. Tetrahedron Lett. 1974, 2257: J. Org. Chem. 1977, 42, 2299.
12. (b) Milstein, D.; Buchman, O.; Blum, J. Tetrahedron Lett. 1974, 2257: J. Org. Chem. 1977, 42, 2299.
13. (c) Alper, H.; Roches, D. D.; Durst, T.; Legault, R. J. Org. Chem. 1976, 41, 3611.
14. (d) Suzuki, M.; Oda, Y.; Noyori, R. J. Am. Chem. Soc. 1979, 101, 1623.
15. (e) Miyashita, A.; Shimada, T.; Sugawara, A.; Norhira, H. Chem. Lett. 1986, 1323.
16. (f) Vankar, Y. D.; Chaudhuri, N. C.; Singh, S. P. Synth. Commun. 1986, 16, 1621.
17. 4. (a) Fry, G. L.; Miraz, T. J. Tetrahedron Lett. 1979, 847.
18. (b) van Tamlene, E. E.; Gladysz, J. A. J. Am. Chem. Soc. 1974, 96, 5290.
19. 5. (a) Curtin, D. Y.; Kellom, D. B. J. Am. Chem. Soc. 1953, 75, 6011.
20. (b) Gurudutt, K. M.; Ravindranath, B. Tetrahedron Lett. 1980, 1173.
21. 6. Halterman, R. L.; McEvoy, M. A. J. Am. Chem. Soc. 1990, 112, 6690.
22. 7. (a) Tsujihara, K.; Furukawa, N.; Oae, K.; Oae, S. Bull. Chem. Soc. Jpn. 1969, 42, 2631.
23. (b) Yasumitsu T.; Bayomi S. M.; Sumoto, M. I. Synthesis 1977, 693.
24. 8. (a) Stork, G.; Jung, M E. J. Am. Chem. Soc. 1974, 96, 3682.
25. (b) Olah, G. A.; Vankar, Y. O.; Arvanaghi, M. Tetrahedron Lett. 1979, 3653.
26. 9. Seitz, W. J.; Sana, A. K.; Hossain, M. M. Organometallics 1993, 12, 2604.
27. 10. King, R. B. J. Inorg. Nucl. Chem. 1963, 25, 1296.
28. 11. The benzylic carbonium ion was also suggested as an intermediate in other transition metal-catalyzed isomerization reactions: see ref. 3.
29. 12. It is more likely that the stable benzylic carbonium ion 6 would form over the less stable methyl carbonium ion in the case of styrene oxide.