Iron(III) tosylate in the preparation of dimethyl and diethyl acetals from ketones and β-keto enol ethers from cyclic β-diketones

Synthetic Communications

Volumn 38, Issue 15, 2008, Pages 2607-2618

  Mansilla, Horacio ^a   Afonso, María M ^b  

^a INSTITUTO DE PRODUCTOS NATURALES Y AGROBIOLOGÍA   (Spain)

^b UNIVERSIDAD DE LA LAGUNA   (Spain)

Author keywords

keto enol ethers; Diethyl acetals; Dimethyl acetals; Iron(III) tosylate; Ketones

Indexed keywords

1,3 DIKETONE; 1,3 DIPHENYLACETONE DIETHYL ACETAL; 1,5 DIPHENYLPENTAN 3 ONE DIETHYL ACETAL; 1,5 DIPHENYLPENTAN 3 ONE DIMETHYL ACETAL; 2 METHYLCYCLOHEXANONE DIETHYL ACETAL; 3 (2 HYDROXYETHOXY) 5,5 DIMETHYL 2 CYCLOHEXEN 1 ONE; 3 (3 HYDROXYPROPOXY) 5,5 DIMETHYL 2 CYCLOHEXEN 1 ONE; 3 (4 HYDROXYBUTOXY) 5,5 DIMETHYL 2 CYCLOHEXEN 1 ONE; 3 CYCLOHEXYLOXY 5,5 DIMETHYL 2 CYCLOHEXEN 1 ONE; 9,9 DIMETHYL 1,4 DIOXASPIRO[4.5]DECAN 7 ONE; ACETAL DERIVATIVE; BENZYLIDENEACETOPHENONE DIETHYL ACETAL; CHLOROACETONE DIETHYL ACETAL; CYCLODODECANON DIETHYL ACETAL; CYCLOHEPTANONE DIETHYL ACETAL; CYCLOOCTANONE DIETHYL ACETAL; ETHER DERIVATIVE; ETHYL 3 ETHOXY 2 BUTENOIC ACID; ETHYL ACETOACETATE DIETHYL ACETAL; IRON DERIVATIVE; KETONE DERIVATIVE; TOLUENESULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ACETALIZATION; ACETYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ETHERIFICATION; METHYLATION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 51349131425     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802219361     Document Type: Article

References (49)

1. (a) Green, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; Wiley: New York, 1999;
2. (b) Meskens, F. A. J. Synthesis 1981, 501.
3. Wenkert, E.; Goodwin, T. E. Synth. Commun. 1977, 7, 409.
4. Hassner, A.; Wiederkehr, R.; Kascheres, J. J. Org. Chem. 1970, 35, 1962.
5. Thurkauf, A.; Jacobson, A. E.; Rice, K. C. Synthesis 1988, 233.
6. Cameron, A. F. B.; Hunt, J. S.; Oughton, J. F.; Wilkinson, P. A.; Wilson, B. M. J. Chem. Soc. 1953, 3864.
7. Anderson, S. H.; Uh, H.-S. Synth. Commun. 1973, 3, 125.
8. Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1980, 21, 1357.
9. Gemal, A. L.; Luche, J.-L. J. Org. Chem. 1979, 44, 4187.
10. Ishihara, K.; Karumi, Y.; Kubota, M.; Yamamoto, H. Synlett 1996, 839.
11. Leonard, N. M.; Oswald, M. C.; Freiberg, D. A.; Nattier, B. A.; Smith, R. C.; Mohan, R. S. J. Org. Chem. 2002, 67, 5202.
12. Srivastava, N.; Dasgupta, S. K.; Banik, B. K. Tetrahedron Lett. 2003, 44, 1191.
13. Surya, K. D.; Gibbs, A. Tetrahedron Lett. 2004, 45, 8141.
14. Clerici, A.; Pastori, N.; Porta, O. Tetrahedron 2001, 57, 217.
15. Smith, B. M.; Graham, E. Tetrahedron Lett. 2006, 47, 9317.
16. Lee, S. H.; Lee, J. H.; Yoon, C. H. Tetrahedron Lett. 2002, 43, 2699.
17. Wu, H. H.; Yang, F.; Cui, P.; Tang, J.; He, M. Y. Tetrahedron Lett. 2004, 45, 4963.
18. Hamada, N.; Kazahaya, K.; Shimizu, H.; Sato, T. Synlett 2004, 1074.
19. Kumar, R.; Chakraborti, K. Tetrahedron Lett. 2005, 46, 8319.
20. Basu, M. K.; Samajdar, S.; Becker, F.; Banik, B. K. Synlett 2002, 319.
21. Bornstein, J.; Bedell, S. F.; Drummond, P. E.; Kosloski, C. L. J. Am. Chem. Soc. 1956, 78, 83.
22. Karimi, B.; Ashtiani, A. M. Chem. Lett. 1999, 1199.
23. Firouzabadi, H.; Iranpoor, N.; Karimi, B. Synlett 1999, 321.
24. Karimi, B.; Seradj, H.; Ebrahimian, G. R. Synlett 1999, 1456.
25. Gopinath, R.; Haque, S. J.; Patel, K. J. Org. Chem. 2002, 67, 5842.
26. Sartori, G.; Ballini, R.; Bigi, F.; Bosica, G.; Maggi, R.; Righi, P. Chem. Rev. 2004, 104, 199.
27. (a) Olah, G. A.; Narang, S. C.; Mediar, D.; Salem, G. F. Synthesis 1981, 282;
28. (b) Patwardhan, S. A.; Dev, S. Synthesis 1974, 348.
29. Taylor, E. C.; Chiang, C. S. Synthesis 1977, 467.
30. Mansilla, H.; Regás, D. Synth. Commun. 2006, 36, 2195.
31. Corma, A.; Climent, M. J.; García, H.; Primo, J. Appl. Catal. 1990, 59, 333.
32. Thomas, B.; Prathapan, S.; Sugunan, S. Micropor. Mesopor. Mat. 2005, 80, 65.
33. Tateiwa, J.; Horiuchi, H.; Uemura, S. J. Org. Chem. 1995, 60, 4039.
34. Tanaka, Y.; Sawamura, N.; Iwamoto, M. Tetrahedron Lett. 1998, 39, 9457.
35. Shimizu, K.; Hayashi, E.; Hatamachi, T.; Kodama, T.; Kitayama, Y. Tetrahedron Lett. 2004, 45, 5135.
36. Holmes, S. M.; McKinley, S. G.; Girolami, G. S. Inorg. Synth. 2002, 23, 91.
37. (a) Marshall, D. R.; Roberts, T. R. J. Chem. Soc. B 1971, 797;
38. (b) House, H.; Rasmusson, G. H. J. Org. Chem. 1963, 28, 27;
39. (c) Takahashi, T.; Tanaka, T.; Suzuki, M.; Hirama, M. Tetrahedron 1994, 50, 1327.
40. (a) Demir, A. S.; Sesenoglu, O. Org. Lett. 2002, 4, 2021;
41. (b) Chen, B. C.; Weismiller, M. C.; Davis, F. A. Tetrahedron 1991, 47, 173.
42. Zimmerman, H. E.; Wang, P. A. J. Am. Chem. Soc. 1993, 115, 2205.
43. Bhosale, R. S.; Bhosale, S. V.; Wang, T.; Zubaidha, P. K. Tetrahedron Lett. 2004, 45, 7187.
44. Chandrasekhar, S.; Rao, Y. S.; Reddy, N. R. Synlett 2005, 1471.
45. Curini, M.; Epifano, F.; Genovese, S. Tetrahedron Lett. 2006, 47, 4697.
46. Banerjee, B.; Mandal, S. K.; Roy, S. C. Chem. Lett. 2006, 35, 16.
47. Das, B.; Laxminarayana, K.; Ravikanth, B. J. Mol. Cat. A: Chem. 2007, 271, 131.
48. (a) Mphahlele, M. J.; Modro, T. A. J. Org. Chem. 1995, 60, 8236.
49. (b) Nelson, P. H.; Nelson, J. T. Synthesis 1992, 1287