The first simple method of protection of hydroxy compounds as their O-Boc derivatives under Lewis acid catalysis

Synlett

Volumn , Issue 13, 2006, Pages 2104-2108

  Bartoli, Giuseppe ^a   Bosco, Marcella ^a   Carlone, Armando ^a   Dalpozzo, Renato ^b   Locatelli, Manuela ^a   Melchiorre, Paolo ^a   Palazzi, Paolo ^a   Sambri, Letizia ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b UNIVERSITY OF CALABRIA   (Italy)

Author keywords

Alcohols; Esterification; Lewis acids; Protecting groups; Zinc acetate

Indexed keywords

ALCOHOL; AROMATIC COMPOUND; HYDROXYL GROUP; LEWIS ACID; ZINC ACETATE;

ARTICLE; CATALYSIS; PROTECTION; RACEMIZATION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 33748268274     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-949609     Document Type: Article

References (36)

1. (a) Parrish, J. P.; Salvatore, R. N.; Jung, K. W. Tetrahedron 2000, 56, 8207.
2. (b) Shaikh, A. A. G.; Sivaram, S. Chem. Rev. 1996, 96, 951.
3. Hegarty, A. F. In Comprehensive Organic Chemistry, Vol. 2; Sutherland, I. O., Ed.; Pergamon: London, 1979, 1067.
4. Some selected references follow: (a) Veldurthy, B.; Clacens, J. M.; Figueras, F. Eur. J. Org. Chem. 2005, 1972.
5. (b) Tundo, P.; Rossi, L.; Loris, A. J. Org. Chem. 2005, 70, 2219.
6. (c) Srivastava, R.; Srinivas, D.; Ratnasamy, P. Appl. Catal., A 2005, 289, 128.
7. (d) Veldurthy, B.; Figueras, F. Chem. Commun. 2004, 734.
8. (e) Bratt, M. O.; Taylor, P. C. J. Org. Chem. 2003, 68, 5439.
9. (f) Carloni, S.; De Vos, D. E.; Jacobs, P. A.; Maggi, R.; Sartori, G.; Sartorio, R. J. Catal. 2002, 205,199.
10. (g) Verdecchia, M.; Feroci, M.; Palombi, L.; Rossi, L. J. Org. Chem. 2002, 67, 8287.
11. (h) Tundo, P.; Selva, M. Acc. Chem. Res. 2002, 35, 706.
12. (i) Salvatore, R. N.; Chu, F.; Nagle, A. S.; Kapxhiu, E. A.; Cross, R. M.; Jung, K. W. Tetrahedron 2002, 58, 3329.
13. Greene, T. W.; Wuts, P. G. M. In Protective Groups in Organic Synthesis, 3rd ed.; Wiley: New York, 1999, 518-525.
14. Ref. 4, page 281.
15. Houlihan, F.; Bouchard, F.; Frechet, J. M.; Willson, C. G. Can. J. Chem. 1985, 65, 153.
16. Basel, Y.; Hassner, A. J. Org. Chem. 2000, 65, 6368.
17. Haight, A. R.; Stoner, E. J.; Peterson, M. J.; Grover, V. K. J. Org. Chem. 2003, 8092.
18. Peri, F.; Binassi, E.; Manetto, A.; Marotta, E.; Mazzanti, A.; Righi, P.; Scardovi, N.; Rosini, G. J. Org. Chem. 2004, 69, 1353.
19. Ouchi, H.; Saito, Y.; Yamamoto, Y.; Takahata, H. Org. Lett. 2002, 4, 585.
20. Chen, C. T.; Kuo, J. H.; Li, C. H.; Barhate, N. B.; Hon, S. W.; Li, T. W.; Chao, S. D.; Liu, C. C.; Li, Y. C.; Chang, I. H.; Lin, J. S.; Liu, C. J.; Chou, Y. C. Org. Lett. 2001, 3, 3729.
21. Chen, C. T.; Kuo, J. H.; Pawar, V. D.; Munot, Y. S.; Weng, S. S.; Ku, C. H.; Liu, C. Y. J. Org. Chem. 2005, 70, 1188.
22. (a) Bartoli, G.; Boeglin, J.; Bosco, M.; Locatelli, M.; Massaccesi, M.; Melchiorre, P.; Sambri, L. Adv. Synth. Catal. 2005, 347, 33.
23. (b) Gooßen, L.; Döhring, A. Adv. Synth. Catal. 2003, 345, 943.
24. Bartoli, G.; Bosco, M.; Locatelli, M.; Marcantoni, E.; Melchiorre, P.; Sambri, L. Synlett 2004, 239.
25. Bartoli, G.; Bosco, M.; Locatelli, M.; Marcantoni, E.; Massaccesi, M.; Melchiorre, P.; Sambri, L. Synlett 2004, 1794.
26. Bartoli, G.; Bosco, M.; Locatelli, M.; Marcantoni, E.; Melchiorre, P.; Sambri, L. Org. Lett. 2004, 7, 427.
27. Unpublished results.
28. 2O = 8:2.
29. 1H NMR spectrum of the crude reaction mixture. Products were then separated by flash chromatography and recovered amounts confirmed the calculated ratio.
30. 1H NMR spectrum of the crude reaction mixture. Products were then separated by flash-chromatography and recovered amounts confirmed the calculated ratio.
31. (a) Molina, P.; Alajarin, M.; Sanchez-Andrada, P. Tetrahedron Lett. 1993, 34, 5155.
32. (b) Dean, C. S.; Tarbell, D. S.; Friedergang, A. W. J. Org. Chem. 1970, 35, 3393.
33. 2O = 8:2.
34. 2O were stirred together for 144 h and only 13% conversion to carbonate was detected by NMR.
35. 1H NMR spectrum of the crude reaction mixture.
36. Nakamura, K.; Nakajima, T.; Kayahara, H.; Nomura, E.; Taniguchi, H. Tetrahedron Lett. 2004, 45, 495.