Reexamination of products and the reaction mechanism of the chalcogeno- Baylis-Hillman reaction: Chalcogenide-TiCl4-mediated reactions of electron- deficient alkenes with aldehydes

Tetrahedron

Volumn 56, Issue 27, 2000, Pages 4725-4731

  Kataoka, Tadashi ^a   Kinoshita, Hironori ^a   Iwama, Tetsuo ^a   Tsujiyama, Shin Ichiro ^a   Iwamura, Tatsunori ^a   Watanabe, Shin Ichi ^a   Muraoka, Osamu ^b   Tanabe, Genzoh ^b  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

^b KINKI UNIVERSITY   (Japan)

Author keywords

Aldols; Enones; Sulfides; Titanium and compounds

Indexed keywords

ALDEHYDE; ALKENE; BENZALDEHYDE DERIVATIVE; CHALCOGEN; DIMETHYL SULFIDE; KETONE; PYRAN DERIVATIVE; SILICA GEL; TITANIUM;

ARTICLE; CHEMICAL REACTION; DIASTEREOISOMER; ELECTRON; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; THIN LAYER CHROMATOGRAPHY; X RAY CRYSTALLOGRAPHY;

EID: 0034733695     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00396-3     Document Type: Article

References (24)

1. Kataoka T., Iwama T., Tsujiyama S. Chem. Commun. 1998;197-198.
2. Drewes, S. E.; Roos, G. H. P. Tetrahedron 1998, 44, 4653-4670; Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001-8062.
3. Drewes, S. E.; Roos, G. H. P. Tetrahedron 1998, 44, 4653-4670; Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001-8062.
4. Kataoka T., Iwama T., Tsujiyama S., Iwamura T., Watanabe S. Tetrahedron. 54:1998;11813-11824.
5. Kataoka T., Iwama T., Kinoshita H., Tsujiyama S., Tsurukami Y., Iwamura T., Watanabe S. Synlett. 1999;197-198.
6. Kataoka T., Iwama T., Tsujiyama S., Kanematsu K., Iwamura T., Watanabe S. Chem. Lett. 1999;257-258.
7. Iwama T., Tsujiyama S., Kinoshita H., Kanematsu K., Tsurukami Y., Iwamura T., Watanabe S., Kataoka T. Chem. Pharm. Bull. 47:1999;956-961.
8. Uehira S., Han Z., Shinokubo H., Oshima K. Org. Lett. 1:1999;1383-1385.
9. Li, G.; Wei, H.-X.; Caputo, T. D. Tetrahedron Lett. 2000, 41, 1-5; Li, G.; Gao, J.; Wei, H.-X.; Enright, M. Org. Lett. 2000, 2, 617-620.
10. Li, G.; Wei, H.-X.; Caputo, T. D. Tetrahedron Lett. 2000, 41, 1-5; Li, G.; Gao, J.; Wei, H.-X.; Enright, M. Org. Lett. 2000, 2, 617-620.
11. Iwama T., Kinoshita H., Kataoka T. Tetrahedron Lett. 40:1999;3741-3744.
12. House, H. O.; Crumrine, D. S.; Teranishi, A. Y.; Olmstead, H. D. J. Am. Chem. Soc. 1973, 95, 3310-3324 and references cited therein.
13. Paterson I., Goodman J.M., Lister M.A., Schumann R.C., McClure C.K., Norcross R.D. Tetrahedron. 46:1990;4663-4684.
14. Heathcock C.H., Pirrung M.C., Sohn J.E. J. Org. Chem. 44:1979;4294-4299.
15. Dubois J.E., Fellmann P. Tetrahedron Lett. 14:1975;1225.
16. Hull C., Mortlock S.V., Thomas E.J. Tetrahedron. 45:1989;1007-1015.
17. Kataoka T., Kinoshita H., Kinoshita S., Iwamura T., Watanabe S. Angew. Chem. 39:2000;. in press.
18. Nakamura E., Kuwajima I. Tetrahedron Lett. 24:1983;3343-3346.
19. Harrison C.R. Tetrahedron Lett. 28:1987;4135-4138.
20. Heathcock C.H., Buse C.T., Kleschick W.A., Pirrung M.C., Sohn J.E., Lampe J. J. Org. Chem. 45:1980;1066-1081.
21. Detty, M. R.; Murray, B. J.; Seidler, M. D. J. Org. Chem. 1982, 47, 1969-1971; Detty, M. R.; Hassett, J. W.; Murray, B. J.; Reynolds, G. A. Tetrahedron 1985, 41, 4853-4859.
22. Detty, M. R.; Murray, B. J.; Seidler, M. D. J. Org. Chem. 1982, 47, 1969-1971; Detty, M. R.; Hassett, J. W.; Murray, B. J.; Reynolds, G. A. Tetrahedron 1985, 41, 4853-4859.
23. SAPI91: Fan Hai-Fu (1991). Structure Analysis Programs with Intelligent Control, Rigaku Corporation, Tokyo, Japan.
24. DIRDIF92: Beurskens, P. T.; Admiraal, G.; Beurskens, G.; Bosman, W. P.; Garcia-Granda, S.; Gould, R. O.; Smits, J. M. M.; Smykalla, C. Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands, 1992.