A mild and efficient synthesis of β-amino alcohols from epoxides using a mesoporous aluminosilicate catalyst

Tetrahedron Letters

Volumn 48, Issue 36, 2007, Pages 6249-6251

  Robinson, Mathew W C ^a   Timms, David A ^a   Williams, Sarah M ^a   Graham, Andrew E ^a  

^a SWANSEA UNIVERSITY   (United Kingdom)

Author keywords

Amino alcohols; Epoxide ring opening; Heterogeneous catalysis; Mesoporous aluminosilicates

Indexed keywords

ALCOHOL; ALUMINUM DERIVATIVE; AMINOALCOHOL; AROMATIC AMINE; BETA AMINOALCOHOL; EPOXIDE; MESOPOROUS ALUMINOSILICATE; SILICATE; UNCLASSIFIED DRUG;

AMINOLYSIS; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; REACTION TIME; RING OPENING; ROOM TEMPERATURE; SUBSTITUTION REACTION; SYNTHESIS;

EID: 34547671898     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.07.030     Document Type: Article

References (31)

1. Cepanec I., Litvić M., Mikuldaš H., Bartolinčić A., and Vinković V. Tetrahedron 59 (2003) 2435-2439
2. Ager D.J., Prakash I., and Schaad D.R. Chem. Rev. 96 (1996) 835-875
3. O'Brien P. Angew. Chem., Int. Ed. 38 (1999) 326-329
4. Li G., Chang H.T., and Sharpless K.B. Angew. Chem., Int. Ed. 35 (1996) 451-455
5. Joossens J., Van der Veken P., Lambeir A.M., Augustyns K., and Haemers A. J. Med. Chem. 47 (2004) 2411-2413
6. Williams P.G., Yoshida W.Y., Moore R.E., and Paul V.J. J. Nat. Prod. 65 (2002) 29-31
7. Rogers G.A., Parsons S.M., Anderson D.C., Nilsson L.M., Bahr B., Kornreich W.D., Kaufman R., Jacobs R.S., and Kirtman B. J. Med. Chem. 32 (1989) 1217-1230
8. Chini M., Crotti P., and Macchia F. J. Org. Chem. 56 (1991) 5939-5942
9. Pachón L.D., Gamez P., van Brussel J.J.M., and Reedijk J. Tetrahedron Lett. 44 (2003) 6025-6027
10. Bradley D., Williams G., and Lawton M. Tetrahedron Lett. 47 (2006) 6557-6560
11. Mai E., and Schneider C. Chem. Eur. J. 13 (2007) 2729-2741
12. Carrée F., Gil R., and Collin J. Tetrahedron Lett. 45 (2004) 7749-7751
13. Yadav J.S., Reddy A.R., Narsaiah A.V., and Reddy B.V.S. J. Mol. Catal. A: Chem. 261 (2007) 207-212
14. Placzek A.T., Donelson J.L., Trivedi R., Gibbs R.A., and De S.K. Tetrahedron Lett. 46 (2005) 9029-9034
15. Kamal A., Adil S.F., and Arifuddin M. Ultrason. Sonochem. 12 (2005) 429-431
16. Kureshy R.I., Singh S., Khan N.H., Abdi S.H.R., Agrawal S., Mayani V.J., and Jasra R.V. Tetrahedron Lett. 47 (2006) 5277-5279
17. Fringuelli F., Pizzo F., Toroolli S., and Vaccaro L. J. Org. Chem. 69 (2004) 7745-7747
18. Horváth A., Skoda-Földes R., Mahó S., Berente Z., and Kollár L. Steroids 71 (2006) 706-711
19. Yadav J.S., Reddy B.V.S., Basak A.K., and Venkat Narsaiah A. Tetrahedron Lett. 44 (2003) 1047-1050
20. Fringuelli F., Pizzo F., Toroolli S., and Vaccaro L. J. Org. Chem. 69 (2004) 7745-7747
21. Azizi N., and Saidi M.R. Org. Lett. 7 (2005) 3649-3651
22. Azizi N., and Saidi M.R. Tetrahedron 63 (2007) 888-891
23. Curini M., Epifano F., Marcotullio M.C., and Rosati O. Eur. J. Org. Chem. (2001) 4149-4152
24. Kureshy R.I., Singh S., Khan N.H., Abdi S.H.R., Suresh E., and Jasra R.V. J. Mol. Catal. A: Chem. 264 (2006) 162-169
25. Chakraborti A.K., Kondasar A., and Rudrawar S. Tetrahedron 60 (2004) 9085-9091
26. Robinson M.W.C., Buckle R., Mabbett I., Grant G.M., and Graham A.E. Tetrahedron Lett. 48 (2007) 4723-4725
27. Robinson M.W.C., and Graham A.E. Tetrahedron Lett. 48 (2007) 4727-4731
28. Lewars E.G. In: Katritzky A.R., Rees C.W., and Lwowski W. (Eds). Comprehensive Heterocyclic Chemistry Vol. 7 (1984), Pergamon, Oxford 100-113
29. Pearson R.G., and Songstad J. J. Am. Chem. Soc. 89 (1967) 1827-1836
30. Bradley D., Williams G., and Lawton M. Tetrahedron Lett. 47 (2006) 6557-6560
31. Our initial results for the mesoporous aluminosilicate promoted Meinwald rearrangement of epoxides will be the subject of a subsequent publication.