Efficient Aerobic Oxidation of Acetals to Esters Catalyzed by N-Hydroxy phthalimide (NHPI) and Co(II) under Mild Conditions

Synthesis

Volumn , Issue 15, 2003, Pages 2373-2377

  Karimi, Babak ^a   Rajabi, Jamshid ^a  

^a INSTITUTE FOR ADVANCED STUDIES IN BASIC SCIENCES IASBS   (Iran)

Author keywords

Catalysis; Esters; Oxidation

Indexed keywords

ACETAL RESINS; CATALYSIS; CATALYSTS; ESTERS;

AEROBIC OXIDATION;

OXIDATION;

1,3 DIOXANE DERIVATIVE; ACETAL; ACETAL DERIVATIVE; COBALT; ESTER; ESTER DERIVATIVE; N HYDROXYPHTHALIMIDE; OXYGEN; PHTHALIMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0242487837     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-42396     Document Type: Article

References (36)

1. (a) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd Ed.; Wiley: New York, 1999.
2. (b) Kocienski, P. J. Protecting Groups; Thieme: Stuttgart, 1994.
3. Larock, R. C. Comprehensive Organic Transformations; VCH: New York, 1999.
4. Chidambaram, N.; Bhat, S.; Chandrasekaran, S. J. Org. Chem. 1992, 57, 5013.
5. Heywood, D. L.; Phillips, B. J. Org. Chem. 1960, 25, 1699.
6. Sviridov, A. F.; Ermolenko, M. S.; Yashunsky, D. V.; Borodkin, V. S.; Kochetkov, N. K. Tetrahedron Lett. 1987, 28, 2835.
7. Bhat, S.; Ramesha, A. R.; Chandrasekaran, S. Synlett 1995, 329.
8. (a) Prugh, J. D.; McCarthy, W. C. Tetrahedron Lett. 1966, 7, 1351.
9. (b) Pearson, R. G. J. Chem. Soc. 1960, 1682.
10. Wright, J. B. J. Am. Chem. Soc. 1955, 77, 4883.
11. Marvell, E. N.; Joncich, M. J. J. Am. Chem. Soc. 1951, 73, 973.
12. Curini, M.; Epifano, F.; Marcotullio, M. C.; Rosati, O. Synlett 1999, 777.
13. Choudary, B. M.; Reddy, P. N. Synlett 1995, 959.
14. Takeda, T.; Watanabe, H.; Kitahara, T. Synlett 1997, 1149.
15. Espenson, J. H.; Zhu, Z.; Zauche, T. H. J. Org. Chem. 1999, 64, 1191.
16. Hosokawa, T.; Imada, Y.; Murahashi, S. I. J. Chem. Soc., Chem. Commun. 1983, 1245.
17. (a) Deslongchamps, P.; Atlani, P. Can. J. Chem. 1974, 52, 3651.
18. (b) Sundararaman, P.; Walker, E. C.; Djerassi, C. Tetrahedron Lett. 1978, 19, 1627.
19. Gopinath, R.; Paital, A. R.; Patel, B. K. Tetrahedron Lett. 2002, 45, 5123.
20. Kuramshin, E. M.; Gumerova, V. K.; Dyachenko, V. A.; Kulak, L. G.; Molyavko, M. A.; Kochinashvili, M. V.; Mufteev, A. F.; Zelotskii, S. S.; Rakhmankulov, D. L. Zh. Obshch. Khim. 1988, 55, 1069; Chem. Abstr. 1989, 110, 192226h.
21. Kuramshin, E. M.; Gumerova, V. K.; Dyachenko, V. A.; Kulak, L. G.; Molyavko, M. A.; Kochinashvili, M. V.; Mufteev, A. F.; Zelotskii, S. S.; Rakhmankulov, D. L. Zh. Obshch. Khim. 1988, 55, 1069; Chem. Abstr. 1989, 110, 192226h.
22. Ishii, Y.; Sakaguchi, S.; Iwahama, T. Adv. Synth. Catal. 2001, 343, 393.
23. Yoshino, Y.; Hayashi, Y.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1997, 62, 6810.
24. Iwahama, T.; Sakaguchi, S.; Ishii, Y. Chem. Commun. 1999, 727.
25. Iwahama, T.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 9059.
26. (a) Isozaki, S.; Nishiwaki, Y.; Sakaguchi, S.; Ishii, Y. Chem. Commun. 2001, 1352.
27. (b) Sakaguchi, S.; Nishiwaki, Y.; Kitamura, T.; Ishii, Y. Angew. Chem. Int. Ed. 2001, 40, 222.
28. Iwahama, T.; Yoshino, Y.; Keitoku, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2000, 65, 6502.
29. Sakaguchi, S.; Takase, T.; Iwahama, T.; Ishii, Y. Chem. Commun. 1998, 2037.
30. Chen, Y.; Wang, P. G. Tetrahedron Lett. 2001, 42, 4955.
31. Cecchetto, A.; Minisci, F.; Recupero, F.; Fontana, F.; Pedulli, G. F. Tetrahedron Lett. 2002, 43, 3605.
32. (a) Sheldon, R. A. ; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981.
33. (b) Basolo, F.; Jones, R. D.; Summerville, D. A. Chem. Rev. 1979, 79, 139.
34. (c) Wong, C. L.; Switer, J. A.; Balakrishnan, K. P.; Endicott, J. F. J. Am. Chem. Soc. 1980, 102, 5511.
35. (d) Drago, R. S.; Cannady, J. P.; Leslie, K. A. J. Am. Chem. Soc. 1980, 102, 6014.
36. (e) Bozell, J. J.; Hames, B. R.; Dimmel, D. R. J. Org. Chem. 1995, 60, 2398.