Abstract
A novel application of Fe–Zn double metal cyanide complexes as solid, acid catalysts for regioselective synthesis of β-amino alcohols under solvent-free conditions via ring-opening of epoxides with amines is reported for the first time. The conversion of epoxides to β-amino alcohols is nearly 100%. In the reaction with styrene oxide, regioselective β-amino alcohol formation is higher with aromatic than with aliphatic amines. Strong Lewis acidic Zn2+ ions in the catalyst are probably the active sites in this reaction.
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References
Mitsunobu O (1991) In: Trost BM, Fleming I (eds) Comprehensive organic synthesis, Vol. 6. Pergamon Press, New York, pp 88
Corey EJ, Zhang F-Y (1999) Angew Chem Int Ed Engl 38:1931
Ager DJ, Prakash I, Schaad DR (1996) Chem Rev 96:835
O’Brien P (1999) Angew Chem Int Ed Engl 38:326
Li G, Chang H-T, Sharpless KB (1996) Angew Chem Int Ed Engl 35:451
Kamal A, Rajendra Prasad B, Malla Reddy A, Naseer M, Khan A (2007) Catal Commun 8:1876
Vijender M, Kishore P, Narender P, Satyanarayana B (2007) J Mol Catal A Chem 266:290
Placzek AT, Donelson JL, Trivedi R, Gibbs RA, De SK (2005) Tetrahedron Lett 46:9029
Iqbal J, Pandey A (1990) Tetrahedron Lett 31:575
Yadav JS, Reddy BVS, Basak AK, Narasaiah AV (2003) Tetrahedron Lett 44:1047
Zhao P-Q, Xu L-W, Xia CG (2004) Synlett 2004:245
Satyarthi JK, Saikia L, Srinivas D, Ratnasamy P (2007) Appl Catal A: Gen 330:145
Saikia L, Satyarthi JK, Srinivas D, Ratnasamy P (2007) J Catal 252:148
van der Hulst H, Pogany GA, Kuyper J (1984) US Patent No. 4,477,589
Kim I, Ahn J-T, Ha C-S, Yang C-S, Park I (2003) Polymer 44:3417
Chen S, Hua Z, Fang Z, Qi G (2004) Polymer 45:6519
Srivastava R, Srinivas D, Ratnasamy P (2006) J Catal 241:34
Sreeprasanth PS, Srivastava R, Srinivas D, Ratnasamy P (2006) Appl Catal A: Gen 314:148
Kureshy RI, Singh S, Khan NH, Abdi SHR, Suresh E, Jasra RV (2007) J Mol Catal A: Chem 264:162
Parker RE, Isaacs NS (1959) Chem Rev 59:737
Acknowledgment
L.S. and J.K.S. acknowledge the Council of Scientific and Industrial Research (CSIR), New Delhi for the award of a research fellowship.
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Saikia, L., Satyarthi, J.K., Gonnade, R. et al. Double Metal Cyanides as Efficient Solid Acid Catalysts for Synthesis of β-Amino Alcohols Under Solvent-Free Conditions. Catal Lett 123, 24–31 (2008). https://doi.org/10.1007/s10562-008-9410-z
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DOI: https://doi.org/10.1007/s10562-008-9410-z