Zirconium sulfophenyl phosphonate as a heterogeneous catalyst in the preparation of β-amino alcohols from epoxides

European Journal of Organic Chemistry

Volumn , Issue 21, 2001, Pages 4149-4152

  Curini, Massimo ^a   Epifano, Francesco ^a   Marcotullio, Maria Carla ^a   Rosati, Ornelio ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

Author keywords

Amines; Amino alcohols; Epoxides; Phosphonate ligands; Zirconium

Indexed keywords

AMINOALCOHOL; BETA AMINOALCOHOL; EPOXIDE; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG; ZIRCONIUM; ZIRCONIUM SULFOPHENYL PHOSPHONATE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; ISOMERISM; METHODOLOGY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0034755750     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200111)2001:21<4149::AID-EJOC4149>3.0.CO;2-R     Document Type: Article

References (20)

1. D. M. Hodgson, A. R. Gibbs, G. P. Lee, Tetrahedron 1996, 25, 14361-14384.
2. S. C. Bergmeier, Tetrahedron 2000, 56, 2561-2576.
3. [3a] G. A. Roger, S. M. Parsons, D. C. Nilsson, L. M. Bahr, W. D. Kornreich, R. Kaufman, R. S. Jacobs, B. Kirtman, J. Med. Chem. 1989, 32, 1217-1230.
4. [3b] B. L. Chng, A. Ganesan, Bioorg. Med. Chem. Lett. 1997, 7, 1511-1514.
5. [4a] J. A. Deyrup, C. L. Moher, J. Org. Chem. 1969, 34, 175-179.
6. [4b] P. A. Crooks, R. Szyudler, Chem. Ind. (London) 1973, 1111-1112.
7. S. Rampalli, S. S. Chaudhari, K. G. Akamanchi, Synthesis 2000, 1, 78-80 and references cited.
8. U. M. Lindström, B. Olofsson, P. Somfai, Tetrahedron Lett. 1999, 40, 9273-9276.
9. M. M. Mojtadei, M. R. Saidi, M. Bolourtchion, J. Chem. Res. (S) 1999, 128-129.
10. G. W. Kobalka, R. M. Pagni, Tetrahedron 1997, 53, 7999-8065 and references cited therein.
11. M. Curini, O. Rosati, E. Pisani, U. Costantino, Synlett. 1996, 333-334.
12. [10a] M. Curini, M. C. Marcotullio, O. Rosati, E. Pisani, U. Costantino, Synlett. 1997, 769-770.
13. [10b] M. Curini, F. Epifano, M. C. Marcotullio, O. Rosati, U. Costantino, Tetrahedron Lett. 1998, 39, 8159-8162.
14. [10c] M. Curini, F. Epifano, M. C. Marcotullio, O. Rosati, U. Costantino, Synthetic Comm. 1999, 541-546.
15. To support this proposal, in a separate experiment we used the catalyst previously treated with an excess of n-butylamine, filtered and dried at 120°C for 12 hours. Treatment of cyclohexene oxide with aniline under standard reaction conditions with this form of catalyst lead to no reaction even after 24 hours.
16. L. Rajender Reddy, M. Arjun Reddy, N. Bhanumathi, K. Rama Rao, Synlett 2000, 3, 339-340.
17. G. Sekar, V. K. Singh, J. Org. Chem. 1999, 64, 287-289.
18. B. Alcaide, C. López-Mardomingo, R. Pérez-Ossorio, J. Plumet, J. Chem. Soc., Perkin Trans. 2 1983, 1649-1653.
19. J. Barluenga, L. Alonso-Cires, G. Asensio, Synthesis 1981, 376-378.
20. The catalyst can be reused several times after washing with dichloromethane and drying at 120°C for 12 hours. The reaction of cyclohexene oxide and aniline (entry 3) has been repeated three times with the following yields: 87% (24 h), 88% (24 h), 85% (24 h).