ZrCl4 as a new and efficient catalyst for the opening of epoxide rings by amines

Tetrahedron Letters

Volumn 44, Issue 45, 2003, Pages 8315-8319

  Chakraborti, Asit K ^a   Kondaskar, Atul ^a  

^a NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

Author keywords

Amine; Epoxide; Regioselectivity; Zirconium

Indexed keywords

AMINE; AMINOALCOHOL; EPOXIDE; STYRENE OXIDE; UNCLASSIFIED DRUG; ZIRCONIUM CHLORIDE; ZIRCONIUM DERIVATIVE;

ARTICLE; CATALYST; RING OPENING; STEREOCHEMISTRY; SYNTHESIS;

EID: 0141922940     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.046     Document Type: Article

References (51)

1. Gehlert D.R., Goldstein D.J., Hipskind P.A. Ann. Rep. Med. Chem. 1999;201-210.
2. Corey E.J., Zhang F. Angew. Chem., Int. Ed. 38:1999;1931-1934.
3. Johannes C.W., Visser M.S., Weatherhead G.S., Hoveyda A.H. J. Am. Chem. Soc. 120:1998;8340-8347.
4. Chng B.L., Ganesan A. Bioorg. Med. Chem. Lett. 7:1997;1511-1514.
5. Rogers G.A., Parsons S.M., Anderson D.C., Nilsson L.M., Bahr B.A., Kornreich W.D., Kaufman R., Jacobs R.S., Kirtman B. J. Med. Chem. 32:1989;1217-1230.
6. De Cree J., Geukens H., Leempoels J., Verhaegen H. Drug Dev. Res. 8:1986;109-117.
7. O'Brien P. Angew Chem., Int. Ed. 38:1999;326-329.
8. Li G., Chang H.-T., Sharpless K.B. Angew Chem., Int. Ed. 35:1996;451-454.
9. Ager D.J., Prakash I., Schaad D.R. Chem. Rev. 96:1996;835-876.
10. Bergmeier S.C. Tetrahedron. 56:2000;2561-2576.
11. Hodgson D.M., Gibbs A.R., Lee G.P. Tetrahedron. 52:1996;14361-14384.
12. Hanson R.M. Chem. Rev. 91:1991;437-475 Mitsunobu, O. In Comprehensive Organic Synthesis; Winterfeldt, E., Ed.; Pergamon Press: New York, 1996; Vol. 6, Part 1.3.4.1.
13. Rao A.S., Paknikar S.K., Kirtane J.G. Tetrahedron. 39:1983;2323-2367.
14. Crooks P.A., Szyudler R. Chem. Ind. (London). 1973;1111-1112.
15. Deyrup J.A., Moyer C.L. J. Org. Chem. 34:1969;175-179.
16. Freifelder M., Stone G.R. J. Org. Chem. 26:1961;1477-1480.
17. Mousseron M., Jullien J., Jolchine Y. Bull. Soc. Chim. Fr. 1952;757-766.
18. Lutz R.E., Freek J.A., Murphy R.S. J. Am. Chem. Soc. 70:1948;2015-2023.
19. Alumina: Posner G.H., Rogers D.Z. J. Am. Chem. Soc. 99:1977;8208-8214.
20. 2AlNHR: Overman L.E., Flippin L.A. Tetrahedron Lett. 22:1981;196-198.
21. Silicon amides: Papini A., Ricci I., Taddei M., Seconi G., Dembach P. J. Chem. Soc., Perkin Trans. 1. 1984;2261-2265.
22. 2NMgBr: Carre M.C., Houmounou J.P., Caubere P. Tetrahedron Lett. 26:1985;3107-3110.
23. 2: Yamada J.-I., Yumoto M., Yamamoto Y. Tetrahedron Lett. 30:1989;4255-4258.
24. Cu amide: Yamamoto Y., Asao N., Meguro M., Tsukade N., Nemoto H., Adayari N., Wilson J.G., Nakamura H. J. Chem. Soc., Chem. Commun. 1993;1201-1203.
25. 4: Sagava S., Abe H., Hase Y., Inaba T. J. Org. Chem. 64:1999;4962.
26. DIPAT (diisopropoxyaluminium trifluoroacetate): Rampalli S., Chaudhari S.S., Akamanchi K.G. Synthesis. 2000;78-80.
27. 4SbOTf: Fujiwara M., Imada M., Baba A., Matsuda H. Tetrahedron Lett. 30:1989;739-742.
28. 3: Chini M., Crotti P., Favero L., Machhia F., Pineschi M. Tetrahedron Lett. 35:1994;433-436.
29. 3: Meguro M., Asao N., Yamamoto Y. J. Chem. Soc., Perkin Trans. 1. 1994;2597-2601.
30. LiOTf: Auge J., Leroy F. Tetrahedron Lett. 37:1996;7715-7716.
31. 2: Sekar G., Singh V.K. J. Org. Chem. 64:1999;287-289.
32. 2: Iqbal J., Pandey A. Tetrahedron Lett. 31:1990;575-576.
33. 5: Chandrasekhar S., Ramchander T., Prakash S.J. Synthesis. 2000;1817-1818.
34. Chini M., Crotti P., Macchia F. Tetrahedron Lett. 31:1990;4661-4664.
35. 2: Weghe V., Collin J. Tetrahedron Lett. 36:1995;1649-1652.
36. 3: Fu X.-L., Wu S.-H. Synth. Commun. 27:1997;1677-1684.
37. 3: Reddy L.R., Reddy M.A., Bhanumathi N., Rao K.R. Synthesis. 2001;831-832.
38. Kotsuki H., Shimanouchi T., Teraguchi M., Kataoka M., Tatsukawa A., Nishizawa H. Chem. Lett. 1994;2159-2162.
39. Kotsuki H., Hayashida K., Shimanouchi T., Nishizawa H. J. Org. Chem. 61:1996;984-990.
40. Mojtahedi M.M., Saidi M.R., Bolourtchian M. J. Chem. Res. (S). 1999;128-129.
41. Metal alkylamides induce the rearrangement of epoxides to allylic alcohols. See: (a) Crandall, J. K.; Apparu, M. Org. React. 1983, 29, 345-443;
42. (b) Kissel, C. L.; Rickborn, B. J. Org. Chem. 1972, 37, 2060-2063.
43. Elkington, J. http://www.sustainability.co.uk/sustainability.htm.
44. Huheey, J. E. Inorganic Chemistry, 3rd ed.; Roger & Harper Row: Singapore, 1990; Chapter 18.
45. rd ed. Clarendon: Oxford, 1988].
46. Moles, P. J. http://www.zrchem.com.
47. Curini M., Epifano F., Marcotullio M.C., Rosati O. Eur. J. Org. Chem. 2001;4149-4152.
48. Anderson S.A., Ayers J.T., DeVries K.M., Ito F., Mendenhall D., Vanderplas B.C. Tetrahedron: Asymmetry. 10:1999;2655-2663.
49. McClure D.E., Arison B.H., Baldwin J.J. J. Am. Chem. Soc. 101:1979;3666-3668.
50. -1] and is not considered poisonous. See: Emsley, J. The Elements, 3rd ed.; Clarendon: Oxford, 1998.
51. Garrett, R. L. In Designing Safer Chemicals; Garrett, R. L.; De Vilto, S. C., Eds.; American Chemical Society Symposium Series 640: Washington DC, 1996; Chapter 1.