The silyl-Prins reaction: A novel method for the synthesis of dihydropyrans

Tetrahedron Letters

Volumn 43, Issue 39, 2002, Pages 7055-7057

  Dobbs, Adrian P ^a   Martinović, Saša ^a  

^a UNIVERSITY OF EXETER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE; DIHYDROPYRAN DERIVATIVE; LEWIS ACID; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; SILYL PRINS REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037163260     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01558-7     Document Type: Article

References (13)

1. Hetero-Diels-Alder reaction: Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press: New York, 1987.
2. . for use of indium catalysts in hetero Diels-Alder reactions; Ali T., Chauhan K.K., Frost C.G. Tetrahedron Lett. 40:1999;5621.
3. Semeyn C., Blaauw R.H., Hiemstra H., Speckamp W.N. J. Org. Chem. 62:1997;3426-3427.
4. Markó I.E., Bayston D.J. Tetrahedron. 50:1994;7141.
5. Markó I.E., Dobbs A.P., Scheirmann V., Chellé F., Bayston D.J. Tetrahedron Lett. 38:1997;2899.
6. Schmidt B., Westhus M. Tetrahedron. 56:2000;2421.
7. de Rosa M., Solladié-Cavallo A., Scettri A. Tetrahedron Lett. 41:2000;1593.
8. Snider, B. B. The prins and carbonyl ene reactions, Chapter 2.1. In Comprehensive Org. Synth., Heathcock, C. H., Vol. 2 (editor-in-Chief B. M. Trost).
9. Viswanathan G.S., Yang J., Li C.-J. Org. Lett. 1:1999;993.
10. Brimble M.A., Pavia G.S., Stevenson R.J. Tetrahedron Lett. 43:2002;1735.
11. Li J., Li C.-J. Tetrahedron Lett. 42:2001;793.
12. 4) and concentrated to an oil that was purified by flash chromatography (typically hexane:ethyl acetate, 4:1) to give the desired product. All compounds were in good agreement with previously reported data or gave satisfactory analytical data.
13. 2), 21.7 (Me).