Mg(ClO4)2, an efficient catalyst for synthesis of β-amino alcohols by ring opening of epoxides with amines under solvent-free conditions

Synthetic Communications

Volumn 41, Issue 4, 2011, Pages 594-602

  Jafari, Abbas Ali ^a   Moradgholi, ^a  

^a YAZD UNIVERSITY   (Iran)

Author keywords

amino alcohols; Amines; epoxides; Mg(ClO4)2; ring opening; solvent free

Indexed keywords

AMINE; AMINOALCOHOL; EPOXIDE; MAGNESIUM PERCHLORATE;

ARTICLE; CATALYST; CHEMICAL REACTION; RING OPENING; ROOM TEMPERATURE; SYNTHESIS;

EID: 79551656129     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911003629473     Document Type: Article

References (31)

1. Parker, R. E.; Isaacs, N. S. Mechanisms of epoxide reactions. Chem. Rev. 1959, 59, 737-799.
2. Bonini, C.; Righi, G. Regio- and chemoselective synthesis of halohydrines by cleavages of oxiranes with metal halides. Synthesis 1994, 225-238.
3. Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Recent advances in the preparation and synthetic applications of oxiranes. Tetrahedron 1983, 39, 2323-2367.
4. Smith, J. G. Synthetically useful reactions of epoxides. Synthesis 1984, 629-656.
5. Ager, D. J.; Prakash, I.; Schaad, D. R. 1,2-Amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis. Chem. Rev. 1996, 96, 835-875.
6. Bose, D. S.; Narsaiah, A. V. An efficient asymmetric synthesis of (S)-atenolol: Using hydrolytic kinetic resolution. Bioorg. Med. Chem. 2005, 627-630.
7. Deyrup, J. A.; Moyer, C. L. 1,2,3-Oxathiazolidines heterocyclic system. J. Org. Chem. 1969, 34, 175-179.
8. Reddy, L. R.; Reddy, M. A.; Bhanumati, N.; Rao, K. R. Cerium chloride-catalysed cleavage of epoxides with aromatic amines. Synthesis 2001, 831-832.
9. 4 as a new and efficient catalyst for the opening of epoxide rings by amines. Tetrahedron Lett. 2003, 44, 8315-8319.
10. 2O as an efficient Lewis acid-surfactant-combined catalyst for organic reactions in water: Efficient conversion of epoxides to thiiranes and to amino alcohols at room temperature. J. Mol. Catal. A: Chem. 2007, 274, 109-115.
11. Zhao, P. Q.; Xu, L. W.; Xia, C. G. Transition metal-based Lewis acid - catalyzed ring opening of epoxides using amines under solvent-free conditions. Synlett 2004, 846-850.
12. Kamal, A.; Ramu, R.; Azhar, M. A.; Khanna, G. B. R. Copper(II) tetrafluoroborate-catalyzed ring-opening of epoxides by amines. Tetrahedron Lett. 2005, 46, 2675-2677.
13. 2O3 as a heterogeneous and recyclable catalyst. Tetrahedron Lett. 2008, 49, 1795-1800.
14. Ollevier, T.; Lavie-Compin, G. Bismuth triflate-catalyzed mild and efficient epoxide opening by aromatic amines under aqueous conditions. Tetrahedron Lett. 2004, 45, 49-52.
15. Procopio, A.; Gaspari, M.; Nardi, M.; Oliverio, M.; Rosati, O. Highly efficient and versatile chemoselective addition of amines to epoxides in water catalyzed by erbium(III) triflate. Tetrahedron Lett. 2008, 49, 2289-2293.
16. 2-catalysed regioselective styrene oxide ring opening with aromatic amines. Tetrahedron 2008, 64, 11732-11737.
17. Ollevier, T.; Nadeau, E. Microwave-enhanced bismuth triflate-catalyzed epoxide opening with aliphatic amines. Tetrahedron Lett. 2008, 49, 1546-1550.
18. Curini, M.; Epifano, F.; Marcotullio, C. M.; Rosati, O. Zirconium sulfophenyl phospho-nate as a heterogeneous catalyst in the preparation of (5-amino alcohols from epoxides. Eur. J. Org. Chem. 2001, 4149-4152.
19. 2O-catalyzed efficient and facile ring-opening reaction of epoxides with aromatic amines. Catal. Commun. 2009, 10, 842-847.
20. Hosseini-Sarvari, M.; Sharghi, H. Sulfamic acid - catalyzed ring opening of epoxides with amines under solvent-free conditions. J. Iran. Chem. Soc. 2008, 5, 384-393.
21. Kureshy, R. I.; Singh, S.; Khan, N. H.; Razi Abdi, S. H.; Suresh, E.; Jasra, R. V. Efficient method for ring opening of epoxides with amines by NaY zeolite under solvent-free conditions. J. Mol. Catal. A: Chem. 2007, 264, 162-169.
22. Reddy, Y. V.; Saraswathy, M.; Rao, B. V.; Shekaram, T. Polymer-supported copper sulphate - promoted aminolysis of epoxides with aromatic amines. Catal. Commun. 2006, 7, 466-471.
23. 3 in the presence of molten TBAB. Tetrahedron Lett. 2004, 45, 3525-3529.
24. 2O-catalyzed regioselective ring opening of epoxides with aliphatic, aromatic, and heteroaro-matic amines. Tetrahedron Lett. 2008, 49, 3672-3676.
25. Kamal, A.; Prasad, B. R.; Reddy, A. M., Khan, M. N. A. Sulfamic acid as an efficient and recyclable catalyst for the ring opening of epoxides with amines and anilines: An easy synthesis of b-amino alcohols under solvent-free conditions. Catal. Commun. 2007, 8, 1876-1880.
26. Chakraborti, A. K.; Kondaskar, A.; Rudrawar, S. Scope and limitations of montmoril-lonite K-10 - catalysed opening of epoxide rings by amines. Tetrahedron 2004, 60, 9085-9091.
27. Tanaka, K.; Toda, F. Solvent-free organic synthesis. Chem. Rev. 2000, 100, 1025-1074.
28. Varma, R. S. Solvent-free organic syntheses using supported reagents and microwave irradiation. Green Chem. 1999, 43-55.
29. Bhagat, S.; Chakraborti, A. K. An extremely efficient three-component reaction of aldehydes/ketones, amines, and phosphites (Kabachnik-Fields reaction) for the synthesis of a-aminophosphonates catalyzed by magnesium perchlorate. J. Org. Chem. 2007, 72, 1263-1270.
30. Wu, J.; Sun, W.; Xia, H.-G.; Sun, X. A facile and highly efficient route to a-amino phosphonates via three-component reactions catalyzed by Mg(ClO4)2 or molecular iodine. Org. Biomol. Chem. 2006, 4, 1663-1666.
31. Bartoli, G.; Bosco, M.; Dalpozzo, R.; Marcantoni, E.; Massaccesi, M.; Rinaldi, S.; Sambria, L. Mg(ClO4)2 as a powerful catalyst for the acylation of alcohols under solvent-free conditions. Synlett 2003, 39-42.