Efficient synthesis of salicylates by catalytic [3 + 3] cyclizations of 1,3-bis(silyl enol ethers) with 1,1,3,3-tetramethoxypropane

Journal of Organic Chemistry

Volumn 72, Issue 16, 2007, Pages 6284-6286

  Sher, Muhammad ^a   Tam Dang, T H ^a   Ahmed, Zafar ^a   Rashid, Muhammad A ^a   Fischer, Christine ^a   Langer, Peter ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

SALICYLIC ACID;

CATALYSIS; CYCLIZATION; ETHERS; PROPANE; SYNTHESIS (CHEMICAL);

CARBOXYLIC ACIDS;

1,1,3,3 TETRAMETHOXYPROPANE; BENZOIC ACID DERIVATIVE; ETHYL 2 HYDROXY 3 METHYLBENZOATE; ETHYL 2 METHOXYBENZOATE; ETHYL 3 METHYLSALICYLATE; PROPANE; SALICYLIC ACID DERIVATIVE; SILANE DERIVATIVE; TITANIUM TETRACHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CONCENTRATION (PARAMETERS); CYCLIZATION; POLYMERIZATION; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE;

CATALYSIS; CHEMISTRY, ORGANIC; CYCLIZATION; ETHERS; ETHYL ETHERS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MODELS, CHEMICAL; PROPANE; SALICYLATES; SALICYLIC ACID;

EID: 34547639928     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070974a     Document Type: Article

References (33)

1. Römpp Lexikon Naturstoffe; Steglich, W., Fugmann, B., Lang-Fugmann, S., Eds.; Thieme: Stuttgart, 1997.
2. (a) Prelog, V.; Würsch, J.; Königsbacher, K. Helv. Chim. Acta 1951, 34, 258.
3. (b) Beringer, M.; Kuntz, I. J. Am. Chem. Soc. 1951, 73, 364.
4. (c) Bertz, S. H.; Dabbagh, G. Angew. Chem. 1982, 94, 317;
5. Angew. Chem., Int. Ed. Engl. 1982, 21, 306.
6. For intramolecular reactions of unsymmetrical derivatives, see: (d) Yamaguchi, M.; Hasebe, K.; Minabi, T. Tetrahedron Lett. 1986, 27, 2401.
7. (e) Gilbreath, S. G.; Harris, C. M.; Harris, T. M. J. Am. Chem. Soc. 1988, 110, 6172 and following publications.
8. (a) Ried, W.; König, E. Liebigs Ann. Chem. 1972, 757, 153.
9. (b) Covarrubias-Zuniga, A. Synth. Commun. 1998, 28, 1525.
10. (c) Covarrubias-Zuniga, A.; Rios-Barrios, E. J. Org. Chem. 1997, 62, 5688.
11. Barton, D. H. R.; Dressaire, G.; Willis, B. J.; Barrett, A. G. M.; Pfeffer, M. J. Chem. Soc., Perkin Trans. 1 1982, 665.
12. See, for example: (a) Danishefsky, S. J.; Singh, R. K.; Gammill, R. B. J. Org. Chem. 1978, 43, 379.
13. (b) Fink, M.; Gaier, H.; Gerlach, H. Helv. Chim. Acta 1982, 65, 2563.
14. Reviews: (a) Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem. 1996, 108, 1482;
15. Angew. Chem., Int. Ed. Engl. 1996, 35, 1380.
16. (b) Bednarski, M. D.; Lyssikatos, J. P. Comprehensive Organic Synthesis: Selectivity, Strategy and Efficiency in Modern Organic Chemistry; Trost, B. M., Ed.; Pergamon: New York, 1991; Vol. 2, 661.
17. (a) Chan, T.-H.; Brownbridge, P. J. Am. Chem. Soc. 1980, 102, 3534.
18. (b) Brownbridge, P.; Chan, T.-H.; Brook, M. A.; Kang, G. J. Can. J. Chem. 1983, 61, 688.
19. (c) Molander, G. A.; Cameron, K. O. J. Am. Chem. Soc. 1993, 115, 830.
20. See, for example: (a) Roberge, G.; Brassard, P. J. Org. Chem. 1981, 46, 4161.
21. (b) Townsend, C. A.; Davis, S. G. J. Chem. Soc., Chem. Commun. 1983, 1420.
22. (c) Sestelo, J. P.; del Mar Real, M.; Sarandeses, L. A. J. Org. Chem. 2001, 66, 1395.
23. (d) Roush, W. R.; Murphy, M. J. Org. Chem. 1992, 57, 6622.
24. (e) Langer, P.; Kracke, B. Tetrahedron Lett. 2000, 4545.
25. For a review of 1,3-bis(silyl enol ethers), see: Langer, P. Synthesis 2002, 441.
26. For a review of [3 + 3] cyclizations of 1,3-bis(silyl enol ethers), see: Feist, H.; Langer, P. Synthesis 2007, 327.
27. (a) Rashid, M. A.; Reinke, H.; Langer, P. Tetrahedron Lett. 2007. 48, 2321.
28. (b) Nguyen, V. T. H.; Appel, B.; Langer, P. Tetrahedron 2006, 62, 7674.
29. (c) Nguyen, V. T. H.; Bellur, E.; Langer, P. Tetrahedron Lett. 2006, 47, 113.
30. Mamat, C.; Büttner, S.; Trabhardt, T.; Fischer, C.; Langer, P. J. Org. Chem. 2007, in press.
31. Murata, S.; Suzuki, M.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 3248.
32. Bellur, E.; Görls, H.; Langer, P. Eur. J. Org. Chem. 2005, 2074.
33. Freifeld, I.; Shojaei, H.; Langer, P. J. Org. Chem. 2006, 71, 4965.