Highly efficient aminolysis of epoxides catalyzed by reusable zirconyl triflate, ZrO(OTf)2

Synthetic Communications

Volumn 39, Issue 3, 2009, Pages 552-561

  Moghadam, Majid ^a   Tangestaninejad, Shahram ^a   Mirkhani, Valiollah ^a   Mohammadpoor Baltork, Iraj ^a   Gorjipoor, Saeedeh ^a   Yazdani, Parvin ^a  

^a UNIVERSITY OF ISFAHAN   (Iran)

Author keywords

Aminolysis; Epoxide; Ring opening; Zirconyl triflate

Indexed keywords

AMINOALCOHOL; BETA AMINOALCOHOL DERIVATIVE; EPOXIDE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG; ZIRCONIUM DERIVATIVE; ZIRCONYL TRIFLATE;

AMINOLYSIS; ARTICLE; CATALYSIS; NONHUMAN; PRODUCT RECOVERY; RING OPENING; ROOM TEMPERATURE;

EID: 61649108179     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802406729     Document Type: Article

References (37)

1. 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.
2. Bergmeier, S. C. The synthesis of vicinal amino alcohols. Tetrahedron 2000, 56, 2561.
3. Chini, M.; Crotti, P.; Macchia, F. Regioalternating selectivity in the metal salt-catalyzed aminolysis of styrene oxide. J. Org. Chem. 1991, 56, 5939.
4. Sekar, G.; Singh, V. K. An efficient method for cleavage of epoxides with aromatic amines. J. Org. Chem. 1999, 64, 287.
5. Ollevier, T.; Lavie-Compin, G. Bismuth triflate-catalyzed mild and efficient epoxide opening by aromatic amines under aqueous conditions. Tetrahedron Lett. 2004, 45, 49.
6. 3-catalyzed ring opening of epoxides with anilines under microwave irradiation. Chem. Lett. 2004, 33, 304.
7. Williams, D. B. G.; Lawton, M. Aluminium triflate: An efficient recyclable Lewis acid catalyst for the aminolysis of epoxides. Tetrahedron Lett. 2006, 47, 6557.
8. 5-catalyzed cleavage of epoxides with aromatic amines. Synthesis 2000, 1817.
9. Reddy, L. R.; Reddy, M. A.; Bhanumathi, N.; Rao, K. R. An efficient method for the ring opening of epoxides with aromatic amines catalysed by indium trichloride. New J. Chem. 2001, 25, 221.
10. Ollevier, T.; Lavie-Compin, G. An efficient method for the ring opening of epoxides with aromatic amines catalyzed by bismuth trichloride. Tetrahedron Lett. 2002, 43, 7891.
11. Sabitha, G.; Reddy, G. S. K. K.; Reddy, K. B.; Yadav, J. S. Vanadium(III) chloride-catalyzed preparation of β-amino alcohols from epoxides. Synthesis 2003, 2298.
12. 4 as a new and efficient catalyst for the opening of epoxide rings by amines. Tetrahedron Lett. 2003, 44, 8315.
13. Rodriguez, J. R.; Navarro, A. Opening of epoxides with aromatic amines promoted by indium tribromide: A mild and efficient method for the synthesis of β-amino alcohols. Tetrahedron Lett. 2004, 45, 7495.
14. Sundararajan, G.; Vijayakrishna, K.; Varghese, B. Synthesis of β-amino alcohols by regioselective ring opening of arylepoxides with anilines catalyzed by cobaltous chloride. Tetrahedron Lett. 2004, 45, 8253.
15. Carree, F.; Gil, R.; Collin, J. Samarium iodides catalyzed meso-epoxides ring opening by aromatic amines. Tetrahedron Lett. 2004, 45, 7749.
16. Placzek, A. T.; Donelson, J. L.; Trivedi, R.; Gibbs, R. A.; De, S. K. Scandium triflate as an efficient and useful catalyst for the synthesis of β-amino alcohols by regioselective ring opening of epoxides with amines under solvent-free conditions. Tetrahedron Lett. 2005, 46, 9029.
17. Chakraborti, A. K.; Kondaskar, A.; Rudrawar, S. Scope and limitations of montmorillonite K 10 catalysed opening of epoxide rings by amines. Tetrahedron 2004, 60, 9085.
18. Augé, J.; Leroy F. Lithium trifluoromethanesulfonate-catalysed aminolysis of oxiranes. Tetrahedron Lett. 1996, 37, 7715.
19. Meguro, M.; Asao, N.; Yamamoto, Y. J. Ytterbium triflate and high pressure-mediated ring opening of epoxides with amines. J. Chem. Soc., Perkin Trans. 1 1994, 2597.
20. Chini, M.; Crotti, P.; Favero, L.; Macchina, F.; Pineschi, M. Lanthanide(III) trifluoromethanesulfonates as extraordinarily effective new catalysts for the aminolysis of 1,2-epoxides. Tetrahedron Lett. 1994, 35, 433.
21. Reddy, L. R.; Reddy, M. A.; Bhanumathi, N.; Rao, K. R. An efficient method for cleavage of epoxides with aromatic amines catalysed by β-cyclodextrin in water. Synlett 2000, 339.
22. 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.
23. Kamal, A.; Ramu, R. R.; Azhar, M. A.; Khanna, G. B. R. Copper(II) tetrafluoroborate-catalyzed ring-opening of epoxides by amines. Tetrahedron Lett. 2005, 46, 2675.
24. Shivani; Pujala, B.; Chakraborti, A. K. Zinc(II) perchlorate hexahydrate catalyzed opening of epoxide ring by amines: Applications to synthesis of (RS)= (R)-propranolols and (RS)=(R)=(S)- Naftopidils. J. Org. Chem. 2007, 72, 3713.
25. Mirkhani, V.; Tangestaninejad, S.; Yadollahi, B.; Alipanah, L. Ammonium decatungstocerate (IV): An efficient catalyst for ring opening of epoxides with aromatic amines. Catal. Lett. 2005, 93.
26. 2O) as an efficient catalyst for aminolysis of epoxides. Synth. Commun. 2004, 20, 3067.
27. Azizi, N.; Saidi, M. R. Highly efficient ring opening reactions of epoxides with deactivated aromatic amines catalyzed by heteropoly acids in water. Tetrahedron 2007, 63, 888.
28. Yadav, J. S.; Reddy, B. V. S.; Basak, A. K.; Narasaiah, A. V. [Bmim]BF4 ionic liquid: A novel reaction medium for the synthesis of β-amino alcohols. Tetrahedron Lett. 2003, 44, 1047.
29. Robinson, M. W. C.; Timms, D. A.; Williams, S. M.; Graham, A. E. A mild and efficient synthesis of β-amino alcohols from epoxides using a mesoporous aluminosilicate catalyst. Tetrahedron Lett. 2007, 48, 6249.
30. Sreedhar, B.; Radhika, P.; Neelima, B.; Hebalkar, N. Regioselective ring opening of epoxides with amines using monodispersed silica nanoparticles in water. J. Mol. Catal. A: Chem. 2007, 272, 159.
31. 2. Catal. Commun. 2007, 8, 1671.
32. Singh, M. C.; Peddinti, R. K. Antimony(III) chloride-catalyzed ring opening of epoxides with anilines. Tetrahedron Lett. 2007, 48, 7354.
33. Reddy, B. M.; Patil, M. K.; Reddy, B. T.; Park, S.-E. Efficient synthesis of β-amino alcohols by regioselective ring-opening of epoxides with anilines catalyzed by sulfated zirconia under solvent-free conditions. Catal. Commun. 2008, 9, 950.
34. Curini, M.; Epifano, F.; Marcotullio, M. C.; Rosati, O. Zirconium sulfophenyl phosphonate as a heterogeneous catalyst in the preparation of β-amino alcohols from epoxides. Eur. J. Org. Chem. 2001, 4149.
35. 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.
36. 2O) as catalysts or reagents in organic synthesis. J. Iran. Chem. Soc. 2008, 5, 159.
37. 2]. J. Organomet. Chem. 2008, 693, 2041.