TiCl4 promoted three component coupling reaction: An efficient method for the substituted tetrahydropyrilidene acetates

Tetrahedron Letters

Volumn 40, Issue 26, 1999, Pages 4751-4754

  Ghosh, Arun K ^a   Kawahama, Reiko ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TETRAHYDROPYRAN DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; STRUCTURE ANALYSIS; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 0033603475     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00811-4     Document Type: Article

References (10)

1. (a) Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V. In Comprehensive Heterocyclic Chemistry II; Pergamon Press: Oxford, 1996; Vol. 5, pp. 390-396.
2. (b) Harmange, J. C.; Figadere, B. Tetrahedron: Asymmetry 1993, 4, 1711.
3. (a) Mukaiyama, T.; Wariishi, K.; Saito, Y.; Hayashi, M.; Kobayashi, S. Chem. Lett. 1988, 1101;
4. (b) Costerousse, G.; Buendia, J.; Toromanoff, E.; Martel, J. Bull. Chem. Soc. Fr. 1978, 355.
5. Ghosh, A. K.; Kawahama, R. Tetrahedron Lett. 1999, 40, 1083.
6. For syntheses of (tetrahydro-2-pyrilidene) and (tetrahydro-2-furylidene) acetates, see: (a) Takahashi, A.; Kirio, Y.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1989, 111, 643;
7. (b) Sauve, G.; Deslongchamps, P. Syn. Commun. 1985, 15, 201;
8. (c) Casty, G. L.; Stryker, J. M. Organometallics 1997, 16, 3083 and references cited therein.
9. All new compounds gave satisfactory spectroscopic and analytical results.
10. The intermediate B can be formed by loss of the substituted ring proton of A, followed by elimination of the resulting neutral dihydropyran under the action of the released protic acid.