TiCl4 promoted three component coupling reaction: A new method for the synthesis of functionalized tetrahydrofurans and tetrahydropyrans

Tetrahedron Letters

Volumn 40, Issue 6, 1999, Pages 1083-1086

  Ghosh, Arun K ^a   Kawahama, Reiko ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLYOXYLIC ACID; TETRAHYDROFURAN DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE; TITANIUM CHLORIDE; TITANIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; SYNTHESIS;

EID: 0033524802     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02633-1     Document Type: Article

References (15)

1. 1. Westley, J. W. Polyether Antibiotics: Naturally Occurring Acid Ionophores, Vol. I and II, Marcel Dekker: New York, 1982.
2. 2. Katritzky, A. R.; Rees, C. W.; and Scriven, E. F. V. In Comprehensive Heterocyclic Chemistry II, Vol. 2. pp 386-392 and Vol. 5. pp 390-396, Pergamon Press: Oxford, 1996. For excellent reviews see: Boivin, T.L. B. Tetrahedron 1987, 43, 3309; Harmange, J. C.; Figadere, B. Tetrahedron: Asymm. 1993, 4, 1711.
3. 2. Katritzky, A. R.; Rees, C. W.; and Scriven, E. F. V. In Comprehensive Heterocyclic Chemistry II, Vol. 2.pp 386-392 and Vol. 5. pp 390-396, Pergamon Press: Oxford, 1996. For excellent reviews see: Boivin, T.L. B. Tetrahedron 1987, 43, 3309; Harmange, J. C.; Figadere, B. Tetrahedron: Asymm. 1993, 4, 1711.
4. 2. Katritzky, A. R.; Rees, C. W.; and Scriven, E. F. V. In Comprehensive Heterocyclic Chemistry II, Vol. 2.pp 386-392 and Vol. 5. pp 390-396, Pergamon Press: Oxford, 1996. For excellent reviews see: Boivin, T. L. B. Tetrahedron 1987, 43, 3309; Harmange, J. C.; Figadere, B. Tetrahedron: Asymm. 1993, 4, 1711.
5. 2. Katritzky, A. R.; Rees, C. W.; and Scriven, E. F. V. In Comprehensive Heterocyclic Chemistry II, Vol. 2.pp 386-392 and Vol. 5. pp 390-396, Pergamon Press: Oxford, 1996. For excellent reviews see: Boivin, T.L. B. Tetrahedron 1987, 43, 3309; Harmange, J. C.; Figadere, B. Tetrahedron: Asymm. 1993, 4, 1711.
6. 3. Mukaiyama, T.; Wariishi, K.; Saito, Y.; Hayashi, M.; Kobayashi, S. Chem. Lett. 1988, 1101.
7. 4. Sugimura, H.; Osumi, K. Tetrahedron Lett. 1989, 30, 1571.
8. 5. Ethyl glyoxylate was purchased from Fluka Chemical Company as a 50% solution by weight in toluene and was distilled according to the literature procedures. See: Evans, D. A.; MacMillan, D. W. C.; Campos, K. R. J. Am. Chem. Soc. 1997, 119, 10859.
9. 4 was purchased from Aldrich Chemical Company, and used as received.
10. 8
11. 8. Clive, D. L. J.; Manning, H. W.; Boivin, T. L. B.; Postema, M. H. D. J. Org. Chem. 1993, 58, 6857.
12. 9. A small amount (15%) of a mixture of α,β-unsaturated ester resulting from dehydration of alcohol 9 was also isolated.
13. 10. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639.
14. 11. All new compounds gave satisfactory spectroscopic and analytical results.
15. 12. Ghosh, A. K.; Thompson, W. J.; Holloway, M. K.; McKee, S. P.; Duong, T. T.; Lee, H. Y.; Munson, P. M.; Smith, A. M.; Wai, J. M.; Darke, P. L.; Zugay, J. A.; Emini, E. A.; Schleif, W. A.; Huff, J. R.; Anderson, P. S. J. Med. Chem. 1993, 36, 2300 and references cited therein.