Water as catalyst and solvent: Tetrahydropyranylation of alcohols in an aqueous medium

Arkivoc

Volumn 2005, Issue 1, 2004, Pages 20-29

  Kavala, Veerababurao ^a   Samal, Akshaya Kumar ^a   Patel, Bhisma K ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY GUWAHATI   (India)

Author keywords

Aqueous medium; Chemoselectivity; Protection; Tetrahydropyranylation

Indexed keywords

ALCOHOL DERIVATIVE; DIHYDROPYRAN ETHER; ETHER DERIVATIVE; HYDROXYL GROUP; PYRAN DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG; WATER;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL INTERACTION; CHEMICAL REACTION; HIGH TEMPERATURE; PKA; PROTON TRANSPORT;

EID: 15544373965     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (39)

1. (a) Breslow, R. Acc. Chem. Res. 1991, 24, 159.
2. (b) Li, C. -J. Chem. Rev. 1993, 93, 2023.
3. (c) Herrmann, W. A.; Kohlpaintner, C. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1524.
4. (d) Lubineau, A.; Auge, J.; Queneau, Y. Synthesis 1994, 741.
5. (e) Li, C. -J. Tetrahedron 1996, 52, 5643.
6. (f) Kobayashi, S. Synlett 1994, 689.
7. (g) Lindström, U. M. Chem. Rev. 2002, 102, 2751.
8. (h) Shu, K.; Kei, M. Acc. Chem. Res. 2002, 35, 209.
9. (i) Okuhara, T. Chem. Rev. 2002, 102, 3641.
10. (j) Pae, A. N. Cho, Y. S. Current Organic Chemistry 2002, 6, 715.
11. (a) Naik, S.; Bhattacharjya, G.; Talukdar, B.; Patel. B. K, Eur. J. Org. Chem., 2004, 1245.
12. (b) Naik, S.; Bhattacharjya, G.; Kavala, V. R.; Patel B. K., Arkivoc, 2004, 55.
13. (a) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; 3rd ed.; John Wiley & Sons: New York, 1999.
14. (b) Kocieński, P. J. Protecting Groups; Georg Thieme Verlag, New York, 1994.
15. Jarowicki, K.; Kocieński, P. J. Chem. Soc., Perkin Trans.1, 2000, 2495.
16. (a) Babu, B. S.; Balasubramanian, K. K. Synlett. 1999, 1261.
17. (b) Curini, M.; Epifano, F.; Marcotullio, M. C.; Rosati, O.; Costantino, U. Tetrahedron Lett. 1998, 38, 8159.
18. (c) Babu, B. S.; Balasubramanian, K. K. Tetrahedron Lett. 1998, 39, 9287.
19. (d) Mineno, T. Tetrahedron Lett. 2002, 43, 7975.
20. (e) Romanelli, G. P.; Baronetti, G.; Thomas, H. J.; Autino, J. C. Tetrahedron Lett. 2002, 43, 7589.
21. (f) Stephens, J. R.; Butler, P. L.; Clow, C. H.; Oswald, M. C.; Smith, R. C.; Mohan, R. S. Eur. J. Org. Chem. 2003, 3827.
22. (g) Ravindranathan, N.; Ramesh, C.; Das, B. Synlett 2001, 1777.
23. (h) Nishiguchi, T.; Hayakawa, S.; Hirasaka, Y.; Saitoh, M. Tetrahedron Lett. 2000, 41, 9843.
24. (i) Pachamuthu, K.; Vankar, Y. D. J. Org. Chem. 2001, 66, 7511.
25. (j) Ranu, B. C.; Saha, M. J. Org. Chem. 1994, 59, 8269.
26. (k) Hon, Y.-S.; Lee, C.-F. Tetrahedron Lett. 1999, 40, 2389.
27. (l) Naik, S.; Gopinath, R.; Patel, B. K. Tetrahedron Lett. 2001, 42, 7679.
28. (m) Nishiguchi, T.; Kawamine, K. Chem. Commun. 1990, 1766.
29. (n) Khan, A. T.; Mondal, E.; Borah, B. M.; Ghosh, S. Eur. J. Org.Chem. 2003, 4113.
30. (o) Namboodiri, V. V.; Varma, R. S. Tetrahedron Lett. 2002, 43, 1143.
31. (p) Karimi, B.; Maleki, J. Tetrahedron Lett. 2002, 43, 5353.
32. (q) Kumar, H. M. S.; Reddy, B. V. S.; Reddy, E. J.; Yadav, J. S. Chem. Lett. 1999, 857.
33. (r) Nishiguchi, T.; Fujisaki, S.; Kuroda, M.; Kajisaki, K.; Saitoh, M. J. Org. Chem. 1998, 63, 8183.
34. (s) Nishiguchi, T.; Kawamine, K.; Ohstuka, T. J. Chem. Soc. Perkin Trans 1 1992, 153.
35. (t) Deka, N.; Sarma, J. C. J. Org. Chem. 2001, 66, 1947.
36. (a) Namboodiri, V. V.; Varma, R. S. Chem. Comm. 2002, 342.
37. (b) Yadav, J. S.; Reddy, B. V. S.; Gnaneshwar, D. New. J. Chem. 2003, 27, 202.
38. (c) Branco, L. C.; Afonso, C. A. M. Tetrahedron 2001, 57, 4405.
39. 3)