MW-assisted Er(OTf)3-catalyzed mild cleavage of isopropylidene acetals in Tricky substrates

Tetrahedron Letters

Volumn 49, Issue 12, 2008, Pages 1961-1964

  Procopio, Antonio ^a   Gaspari, Marco ^a   Nardi, Monica ^b   Oliverio, Manuela ^a   Romeo, Roberto ^c  

^a UNIVERSITY MAGNA GRAECIA OF CATANZARO   (Italy)

^b UNIVERSITY OF CALABRIA   (Italy)

^c UNIVERSITY OF MESSINA   (Italy)

Author keywords

Erbium(III) triflate; Isopropylidene acetal; MW assisted synthesis; Water as solvent

Indexed keywords

ACETAL DERIVATIVE; ERBIUM; LEWIS ACID; SOLVENT; TRIFLUOROMETHANESULFONIC ACID; WATER;

ARTICLE; CATALYST; SYNTHESIS;

EID: 39249084384     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.01.089     Document Type: Article

References (52)

1. Greene T.W., and Wuts P.G.M. Protecting Groups in Organic Synthesis. 3rd ed. (1999), Wiley & Sons, New York
2. Kocienski P.J. Protecting Groups (2004), Georg Thieme, New York
3. Barone G., Bedini E., Iadonisi A., Manzo E., and Parrilli M. Synlett (2002) 1645-1648
4. Ramalingam T., Srinivas R., Reddy B.V.S., and Yadav J.S. Synth. Commun. 31 (2001) 1091-1095
5. Chen M.-Y., Lu K.C., Lee A.S.-Y., and Lin C.-C. Tetrahedron Lett. 43 (2002) 2777-2780
6. Chen M.-Y., Patkar L.N., Lu K.C., Lee A.S.-Y., and Lin C.-C. Tetrahedron 60 (2004) 11465-11475
7. Steel P.G. J. Chem. Soc., Perkin Trans. 1 (2001) 2727-2751
8. Kobayashi S., and Manabe K. Acc. Chem. Res 35 (2002) 209-217
9. Kobayashi S., Sugiura M., Kitagawa H., and Lam W.W.-L. Chem. Rev. 102 (2002) 2227-2302
10. Dalpozzo R., De Nino A., Maiuolo L., Procopio A., Tagarelli A., Sindona G., and Bartoli G. J. Org. Chem. 67 (2002) 9093-9095
11. Dalpozzo R., De Nino A., Maiuolo L., Nardi M., Procopio A., and Tagarelli A. Synthesis (2004) 496-498
12. Marcantoni E., Nobili F., Bartoli G., Bosco M., and Sambri L. J. Org. Chem. 62 (1997) 4183-4184
13. Carrigan M.D., Sarapa D., Smith R.C., Wieland L.C., and Mohan R.S. J. Org. Chem. 67 (2002) 1027-1030
14. Yan M.-C., Chen Y.-N., Wu H.-T., Lin C.-C., Chen C.-T., and Lin C.-C. J. Org. Chem. 72 (2007) 299-302
15. Bartoli G., Cupone G., Dalpozzo R., De Nino A., Maiuolo L., Marcantoni E., and Procopio A. Synlett (2001) 1897-1900
16. Bartoli G., Cupone G., Dalpozzo R., De Nino A., Maiuolo L., Procopio A., Sambri L., and Tagarelli A. Tetrahedron Lett. 43 (2002) 5945-5947
17. Dalpozzo R., De Nino A., Maiuolo L., Procopio A., Nardi M., Bartoli G., and Romeo R. Tetrahedron Lett. 44 (2003) 5621-5624
18. Bartoli G., Bosco M., Dalpozzo R., Macantoni E., Massaccesi M., Rivalsi S., and Sambri L. Synlett (2003) 39-42
19. De Nino A., Dalpozzo R., Nardi M., Procopio A., Sindona G., and Tagarelli A. Synlett (2004) 2633-2635
20. Procopio A., Dalpozzo R., De Nino A., Maiuolo L., Russo B., and Sindona G. Adv. Synth. Catal. 346 (2004) 1465-1470
21. Procopio A., Dalpozzo R., De Nino A., Maiuolo L., Nardi M., and Russo B. Adv. Synth. Catal. 347 (2005) 1447-1450
22. Procopio A., Dalpozzo R., De Nino A., Maiuolo L., Nardi M., and Romeo G. Org. Biomol. Chem. 3 (2005) 4129-4133
23. Dalpozzo R., De Nino A., Nardi M., Russo B., and Procopio A. Synthesis 2 (2006) 1127-1129
24. Bartoli G., Dalpozzo R., De Nino A., Maiuolo L., Nardi M., Procopio A., and Tagarelli A. Green Chem. 6 (2004) 191-192
25. De Nino A., Dalpozzo R., Maiuolo L., Procopio A., Tagarelli A., and Bartoli G. Eur. J. Org. Chem. (2004) 2176-2180
26. Gedye R., Smith F., Westaway K., Ali H., Baldisera L., Laberge L., and Rousell J. Tetrahedron Lett. 27 (1986) 279-282
27. Giguere R.J., Bray T.L., Duncan S.M., and Majetich G. Tetrahedron Lett. 27 (1986) 4945-4948
28. Loupy A. Microwaves in Organic Synthesis (2002), Wiley-VCH, Weinheim
29. Lidstöm P., and Tierney J.P. Microwave-assisted Organic Synthesis (2005), Blackwell Scientific
30. Kappe C.O., and Stadler A. Microwaves in Organic and Medicinal Chemistry (2005), Wiley-VCH, Weinheim
31. Kappe C.O. Angew. Chem. Int. Ed. 43 (2004) 6250-6284
32. Caddick S. Tetrahedron 51 (1995) 10403-10432
33. Galema S.A. Chem. Soc. Rev. 26 (1997) 233-238
34. Lidström P., Tierney J., Wathey B., and Westman J. Tetrahedron Lett. 57 (2001) 9225-9283
35. Nüchter M., Ondruschka B., Bonrath W., and Gym A. Green Chem. 6 (2004) 128-141
36. Roberts B.A., and Strauss C.R. Acc. Chem. Res. 38 (2005) 653-661
37. Kremsner J.M., and Kappe C.O. Eur. J. Org. Chem. (2005) 3672-3679
38. Dallinger D., and Kappe C.O. Chem. Rev. 107 (2007) 2563-2591
39. Procopio A., Gaspari M., Nardi M., Oliverio M., Tagarelli A., and Sindona G. Tetrahedron Lett. 48 (2007) 8623-8627
40. Tripathi S., Singha K., Achari B., and Mandal S.B. Tetrahedron 60 (2004) 4959-4965
41. Glomb M.A., and Pfahler C. Carbohydr. Res. 329 (2000) 515-523
42. Michael J.P., de Koening C.B., Petersen R.L., and Stranbury T.V. Tetahedron Lett. 42 (2001) 7513-7516
43. Hotchkiss D.J., Jenkinson S.F., Storer R., Heinz T., and Fleet G.W.J. Tetrahedron Lett. 47 (2006) 315-318
44. Jeong B.-S., Choi N.S., Ahn S.K., Bae H., Kim H.S., and Kim D. Bioorg. Med. Chem. Lett. 15 (2005) 3580-3583
45. Cook A.F., and Holman M.J. J. Med. Chem. 22 (1979) 1330-1333
46. Larder B.A., Kellam P., and Kemp S.D. Nature 365 (1993) 451-453
47. Collier A.C., Coombs R.W., Schoenfeld D.A., Bassett R.L., Timpone J., Baruch A., Jones M., Facey K., Whitacre C., McAuliffe V.J., Friedman H.M., Merigan T.C., Reichman R.C., Hooper C., and Corey L. New Engl. J. Med. 334 (1996) 1011-1018
48. Reijers M.H.E., Weverling G.J., Jurriaans S., Wit F.W., Weigel H.M., Kate R.W.T., Mulder J.W., Frissen P.H.J., van Leeuwen R., Reiss P., Schuitemaker H., de Wolf F., and Lange J.M.A. Lancet 352 (1998) 185-190
49. van Praag R.M., Wit F.W., Jurriaans S., de Wolf F., Prins J.M., and Lange J.M.A. AIDS 16 (2002) 719-725
50. Ribes C., Falomir E., and Murga J. Tetrahedron 62 (2006) 1239-1244
51. Yan M.-C., Chen Y.-N., Wu H.-T., Lin C.-C., Chen C.-T., and Lin C.-C. J. Org. Chem. 72 (2007) 299-302
52. 3 in the teflon reaction vessel of a Synthos 3000 microwave synthesizer and the teflon tube tapped and stirred at 120 °C for 5 min under MW irradiation (1000 W). After 5 min, the deprotection was completed and the yield was determined by HPLC using the standard addition method. The evaporation of water solution furnished the crude product, which could be purified by flash-chromatography.