Mg(ClO₄)₂, an Efficient Catalyst for Synthesis of β-Amino Alcohols by Ring Opening of Epoxides with Amines under Solvent-Free Conditions

REFERENCES

• Parker, R. E., and Isaacs, N. S., 1959. Mechanisms of epoxide reactions, Chem. Rev. 59 (1959), pp. 737–799.
   Web of Science ®Google Scholar
• Bonini, C., and Righi, G., 1994. Regio- and chemoselective synthesis of halohydrines by cleavages of oxiranes with metal halides, Synthesis (1994), pp. 225–238.
   Web of Science ®Google Scholar
• Rao, A. S., and Paknikar, S. K.Kirtane, J. G., , 1983. Recent advances in the preparation and synthetic applications of oxiranes, Tetrahedron 39 (1983), pp. 2323–2367.
   Web of Science ®Google Scholar
• Smith, J. G., 1984. Synthetically useful reactions of epoxides, Synthesis (1984), pp. 629–656.
   Web of Science ®Google Scholar
• Ager, D. J., Prakash, I., and Schaad, D. R., 1996. 1,2-Amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis, Chem. Rev. 96 (1996), pp. 835–875.
   PubMed Web of Science ®Google Scholar
• Bose, D. S., and Narsaiah, A. V., 2005. An efficient asymmetric synthesis of (S)-atenolol: Using hydrolytic kinetic resolution, Bioorg. Med. Chem. (2005), pp. 627–630.
   PubMed Web of Science ®Google Scholar
• Deyrup, J. A., and Moyer, C. L., 1969. 1,2,3-Oxathiazolidines heterocyclic system, J. Org. Chem. 34 (1969), pp. 175–179.
   Web of Science ®Google Scholar
• Reddy, L. R., Reddy, M. A., Bhanumati, N., and Rao, K. R., 2001. Cerium chloride–catalysed cleavage of epoxides with aromatic amines, Synthesis (2001), pp. 831–832.
   Web of Science ®Google Scholar
• Chakraborti, A. K., and Kondaskar, A., 2003. ZrCl4 as a new and efficient catalyst for the opening of epoxide rings by amines, Tetrahedron Lett. 44 (2003), pp. 8315–8319.
   Web of Science ®Google Scholar
• Firouzabadi, H., Iranpoor, N., and Khoshnood, A., 2007. Aluminum tris (dodecyl sulfate) trihydrate Al(DS)3 · 3H2O 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. 274 (2007), pp. 109–115.
   Web of Science ®Google Scholar
• Zhao, P. Q., Xu, L. W., and Xia, C. G., 2004. Transition metal–based Lewis acid – catalyzed ring opening of epoxides using amines under solvent-free conditions, Synlett (2004), pp. 846–850.
   Web of Science ®Google Scholar
• Kamal, A., Ramu, R., Azhar, M. A., and Khanna, G. B. R., 2005. Copper(II) tetrafluoroborate–catalyzed ring-opening of epoxides by amines, Tetrahedron Lett. 46 (2005), pp. 2675–2677.
   Web of Science ®Google Scholar
• Maheswara, M., Rao, K. S. V. K., and Do, J. Y., 2008. Regioselective ring opening of epoxides with amines using Zn(ClO4)2–Al2O3 as a heterogeneous and recyclable catalyst, Tetrahedron Lett. 49 (2008), pp. 1795–1800.
   Web of Science ®Google Scholar
• Ollevier, T., and Lavie-Compin, G., 2004. Bismuth triflate–catalyzed mild and efficient epoxide opening by aromatic amines under aqueous conditions, Tetrahedron Lett. 45 (2004), pp. 49–52.
   Web of Science ®Google Scholar
• Procopio, A., Gaspari, M., Nardi, M., Oliverio, M., and Rosati, O., 2008. Highly efficient and versatile chemoselective addition of amines to epoxides in water catalyzed by erbium(III) triflate, Tetrahedron Lett. 49 (2008), pp. 2289–2293.
   Web of Science ®Google Scholar
• Mancilla, G., Femenıa-Rıos, M., Macıas-Sanchez, A. J., and Collado, I. G., 2008. Sn(OTf)2-catalysed regioselective styrene oxide ring opening with aromatic amines, Tetrahedron 64 (2008), pp. 11732–11737.
   Web of Science ®Google Scholar
• Ollevier, T., and Nadeau, E., 2008. Microwave-enhanced bismuth triflate–catalyzed epoxide opening with aliphatic amines, Tetrahedron Lett. 49 (2008), pp. 1546–1550.
   Web of Science ®Google Scholar
• Curini, M., Epifano, F., Marcotullio, C. M., and Rosati, O., 2001. Zirconium sulfophenyl phosphonate as a heterogeneous catalyst in the preparation of β-amino alcohols from epoxides, Eur. J. Org. Chem. (2001), pp. 4149–4152.
   Web of Science ®Google Scholar
• Danafar, H., and Yadollahi, B., 2009. (TBA)4PFeW11O39 · 3H2O-catalyzed efficient and facile ring-opening reaction of epoxides with aromatic amines, Catal. Commun. 10 (2009), pp. 842–847.
   Web of Science ®Google Scholar
• Hosseini-Sarvari, M., and Sharghi, H., 2008. Sulfamic acid – catalyzed ring opening of epoxides with amines under solvent-free conditions, J. Iran. Chem. Soc. 5 (2008), pp. 384–393.
   Web of Science ®Google Scholar
• Kureshy, R. I., Singh, S., Khan, N. H., Razi Abdi, S. H., Suresh, E., and Jasra, R. V., 2007. Efficient method for ring opening of epoxides with amines by NaY zeolite under solvent-free conditions, J. Mol. Catal. A: Chem. 264 (2007), pp. 162–169.
   Web of Science ®Google Scholar
• Reddy, Y. V., Saraswathy, M., Rao, B. V., and Shekaram, T., 2006. Polymer-supported copper sulphate – promoted aminolysis of epoxides with aromatic amines, Catal. Commun. 7 (2006), pp. 466–471.
   Web of Science ®Google Scholar
• Khodaei, M. M., Khosropour, A. R., and Ghozati, K., 2004. A powerful, practical, and chemoselective synthesis of 2-anilinoalkanols catalyzed by Bi(TFA)3 or Bi(OTf)3 in the presence of molten TBAB, Tetrahedron Lett. 45 (2004), pp. 3525–3529.
   Web of Science ®Google Scholar
• Bhanushali, M. J., Nandurkar, N. S., and Bhor, M. D.Bhanage, B. M., , 2008. Y(NO3)3 · 6H2O-catalyzed regioselective ring opening of epoxides with aliphatic, aromatic, and heteroaromatic amines, Tetrahedron Lett. 49 (2008), pp. 3672–3676.
   Web of Science ®Google Scholar
• Kamal, A., Prasad, B. R., Reddy, A. M., and Khan, M. N. A., 2007. Sulfamic acid as an efficient and recyclable catalyst for the ring opening of epoxides with amines and anilines: An easy synthesis of β-amino alcohols under solvent-free conditions, Catal. Commun. 8 (2007), pp. 1876–1880.
   Web of Science ®Google Scholar
• Chakraborti, A. K., Kondaskar, A., and Rudrawar, S., 2004. Scope and limitations of montmorillonite K-10 – catalysed opening of epoxide rings by amines, Tetrahedron 60 (2004), pp. 9085–9091.
   Web of Science ®Google Scholar
• Tanaka, K., and Toda, F., 2000. Solvent-free organic synthesis, Chem. Rev. 100 (2000), pp. 1025–1074.
   PubMed Web of Science ®Google Scholar
• Varma, R. S., 1999. Solvent-free organic syntheses using supported reagents and microwave irradiation, Green Chem. (1999), pp. 43–55.
   Web of Science ®Google Scholar
• Bhagat, S., and Chakraborti, A. K., 2007. An extremely efficient three-component reaction of aldehydes/ketones, amines, and phosphites (Kabachnik–Fields reaction) for the synthesis of α-aminophosphonates catalyzed by magnesium perchlorate, J. Org. Chem. 72 (2007), pp. 1263–1270.
   PubMed Web of Science ®Google Scholar
• Wu, J., Sun, W., Xia, H.-G., and Sun, X., 2006. A facile and highly efficient route to α-amino phosphonates via three-component reactions catalyzed by Mg(ClO4)2 or molecular iodine, Org. Biomol. Chem. 4 (2006), pp. 1663–1666.
   PubMed Web of Science ®Google Scholar
• Bartoli, G., Bosco, M., Dalpozzo, R., Marcantoni, E., Massaccesi, M., Rinaldi, S., and Sambria, L., 2003. Mg(ClO4)2 as a powerful catalyst for the acylation of alcohols under solvent-free conditions, Synlett (2003), pp. 39–42.
   Web of Science ®Google Scholar