Cadmium chloride-catalyzed regioselective opening of oxiranes with aromatic amines - An improved protocol for the synthesis of 2-amino alcohols

Canadian Journal of Chemistry

Volumn 85, Issue 1, 2007, Pages 37-41

  Kumar, S Ramesh ^a   Leelavathi, P ^a  

^a OSMANIA UNIVERSITY   (India)

Author keywords

2 amino alcohols; Aromatic amines; Cadmium chloride; Epoxides

Indexed keywords

ALCOHOLS; AMINES; CADMIUM COMPOUNDS; CATALYST ACTIVITY; REACTION KINETICS; SYNTHESIS (CHEMICAL);

AMINO ALCOHOLS; AROMATIC AMINES; CADMIUM CHLORIDE; RING OPENING REACTION;

PARAFFINS;

EID: 34247891552     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/V06-186     Document Type: Article

References (28)

1. (a) T. Kino, H. Halanaka, M. Hashimoto, M. Nishiyama, T. Goto, M. Okuhara, M. Kohsaka, H. Aoki, and H. Imanaka. J. Antibiot. 40, 1249 (1987);
2. (b) D.S. Bose and A.V. Narsaiah. Bioorg Med. Chem. 3, 627 (2005);
3. (c) E.J. Corey and X-M. Cheng. The logic of chemical synthesis. John Wiley, New York. 1989;
4. (d) P.W. Erhardt, C.M. Woo, W.G. Anderson, and R.J. Gorczynski. J. Med. Chem. 25, 1408 (1982);
5. (f) A.V. Narsaiah. Synth. Commun. 1897 (2006).
6. (a) M. Curini, F. Epifano, M.C. Marcotullio, and O. Rosati. Eur. J. Org. Chem. 4149 (2001);
7. (b) L.D. Pachon, P. Gamez, J.J.M. Van Bessel, and J. Reedijk. Tetrahedron Lett. 44, 6025 (2003);
8. (c) M.M. Khodaei, A.R. Khosropour, and K. Ghozati. Tetrahedron Lett. 45, 3525 (2004);
9. (d) T. Ollevier and G. Lavie- Compin. Tetrahedron Lett. 45, 49 (2004);
10. (e) Y. Yamamoto, N. Asao, M. Meguro, N. Tsukade, H. Nemoto, N. Adayari, J.G. Wilson, and H. Nakamura. J. Chem. Soc., Chem. Commun. 1201 (1993);
11. (f) A.K. Chakraborthi and A. Kondaskar. Tetrahedron Lett. 44, 8315 (2003);
12. (g) N.R. Swamy, G. Kondaji, and K. Nagaiah. Synth. Commun. 32, 2307 (2002);
13. (h) L.R. Reddy, M.A. Reddy, N. Bhanumathi, and K.R. Rao. New J. Chem. 25, 221 (2001);
14. (i) A.K. Chakraborti and A. Kondaskar. Tetrahedron Lett. 44, 8315 (2003);
15. (j) E. Rafiee, S. Tangestaninejad, M.H. Habibi, and V. Mirkhani. Synth. Commun. 36, 3673 (2004);
16. (k) A. McCluskey, S.K. Leitch, J. Garner, C.E. Caden, T.A. Hill, L.R. Odell, and S.G. Stewart. Tetrahedron Lett. 46, 8229 (2005);
17. (l) R.I. Kuteshy, S. Singh, N. Khan, S.H.R. Abdi, E. Suresh, and R.V. Jasra. Eur. J. Org. Chem. 1303 (2006);
18. (m) A.K. Chakraborti, S. Rudrawar, and A. Kondaskar. Eur. J. Org. Chem. 3597 (2004).
19. (n) A. Kamal, R. Ramu, M.A. Azar, and G.B.R. Khanna. Tetrahedron Lett. 46, 2675 (2005);
20. (o) G. Sekar and V.K.J. Singh. Org. Chem. 64, 287 (1999);
21. (p) F. Carrée, R. Gil, and J. Collin. Org. Lett. 7, 1023 (2005);
22. (q) J.S. Yadav, A.R. Reddy, A.V. Narsaiah, and B.V.S. Reddy. J. Mol. Catal. A, 261, 207 (2006).
23. (a) J.S. Yadav, B.V.S. Reddy, A.K. Basak, and A.V. Narsaiah. Tetrahedron Lett. 44, 1047 (2003);
24. (b) J.S. Yadav, B.V.S. Reddy, K. Sadashiv, K. Harikishan, and A.V. Narsaiah. J. Mol. Catal. A, 220, 153 (2004).
25. (a) J.K. Whitesel and S.W. Felman. J. Org. Chem. 45, 755 (1980);
26. (b) J. Yamada, Y. Yomoto, and Y. Yamamoto. Tetrahedron Lett. 30, 4255 (1989).
27. A.V. Narsaiah and K. Nagaiah. Synthesis, 1253 (2004).
28. S. Ramesh Kumar and P. Leelavathi. J. Mol. Catal A, 240, 99 (2005).