Photochemical carbon skeletal rearrangement of the Baylis-Hillman products: β-C-H activation leading to furans

Synlett

Volumn , Issue 5, 1998, Pages 469-470

  Matsumoto, Shoji ^a   Mikami, Koichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002977369     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1715     Document Type: Article

References (20)

1. Mattay, J.; Griesbeck, A. G. Photochemical Key Steps in Organic Synthesis; VCH: New York, 1994.
2. Gilbert, A.; Baggott, J. Essentials of Molecular Photochemistry; Blackwell Scientific: Oxford, 1991.
3. Koizumi, M.; Kato, S.; Malaga, N.; Matsuura, T.; Usui, Y. Photosensitized Reactions; Kagakudojin: Kyoto, 1978.
4. Wagner, P. J.; Park, B. -S. Org. Photochem. 1991, 11, 227.
5. Porco, J. A., Jr.; Schreiber, S. L. in Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I. Eds.; Pergamon: London, 1991; Vol. 5, 151.
6. Schuster, D. I. Chem. Enones 1989, 2, 623.
7. Sauers, R. R.; Edberg, L. A. J. Org. Chem. 1994, 59, 7061.
8. Wanger, P. J. Acc. Chem. Res. 1971, 4, 168.
9. Matsumoto, S.; Okubo, Y.; Mikami, K. J. Am. Chem. Soc. in press.
10. Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 53, 8001.
11. Drewers, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653.
12. The rarity of β-hydrogen abstraction is generally believed to reflect a geometric problem. Cyclic system in a favorable geometry for β-hydrogen abstraction: Scheffer, J. R.; Dzakpasu, A. A. J. Am. Chem. Soc. 1978, 100, 2164.
13. For a similar reaction of 3-methylene-4-phenoxy-2-butanone leading to methyl phenoxycyclopropoxyl ketone (17% yield), see: Cormier. R. A.; Schreiber, W. L.; Agosta, W. C. J. Am. Chem. Soc. 1973, 95, 4873.
14. Wienand, A.; Reissig, H. -U. Organometallics 1990, 9, 3133.
15. Wenkert, E. Acc. Chem. Res. 1980, 13, 27.
16. Review: Padwa, A.; Murphree, S. S. Org. Prep. Proced. Inter. 1991, 23, 545.
17. Koga, Y.; Kusama, H.; Narasaka, K. Bull. Chem. Soc. Jpn. 1998, 71, 475.
18. Mukherjee, A. K.; Agosta, W. C. J. Chem. Soc., Chem. Commun. 1994, 1821.
19. Wakabayashi, Y.; Fukuda, Y.; Shiragami, H.; Utimoto, K.; Nozaki, H. Tetrahedron 1985, 41, 3655.
20. Verhé, R.; de Kimpe, N.; Courtheyn, D.; de Buyck, L. Tetrahedron 1982, 38, 3649.