Synthesis of β,β-branched β-amino ester derivatives through spiroaziridination of (α-trimethylsilanylmethyl)cyclohexylidene esters

Tetrahedron Letters

Volumn 44, Issue 46, 2003, Pages 8467-8470

  Gasperi, Tecla ^a   Loreto, M Antonietta ^a   Tardella, P Antonio ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

Allysilanes; Aziridines; amino esters

Indexed keywords

CALCIUM OXIDE; ESTER DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; SPIROAZIRIDINATION; STEREOCHEMISTRY;

EID: 0141991215     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.093     Document Type: Article

References (48)

1. Seebach D., Abele S. Eur. J. Org. Chem. 2000;1-15. and references cited therein.
2. Helms G.L., Moore R.E., Niemczura W.P., Patterson G.M.L., Tomer K.B., Gross M.L. J. Org. Chem. 53:1988;1298-1307.
3. Hecht S.M. Acc. Chem. Res. 19:1986;383-391.
4. Chu K.S., Negrete G.R., Konopelski J.P. J. Org. Chem. 56:1991;5196-5201.
5. Sone H., Nemoto T., Ishiwata H., Ojika M., Yamada K. Tetrahedron Lett. 34:1993;8449-8452.
6. Reddy S.H.K., Lee S., Datta A., Georg G.I. J. Org. Chem. 66:2001;8211-8214. and references cited therein.
7. Seebach D., Gademann K., Ernst M., Hoyer D. Angew. Chem., Int. Ed. Engl. 38:1999;1223-1226.
8. Bergmeier S.C., Stanchina D.M. J. Org. Chem. 64:1999;2852-2859. and references cited therein.
9. Davies S.G., Dixon D.J. J. Chem. Soc., Perkin Trans. 1. 1998;2635-2643.
10. Palomo C., Aizpurua J.M., Cuevas C. J. Chem. Soc., Chem. Commun. 1994;1957-1958.
11. Nicolaou K.C., Dai W.M., Guy R.K. Angew. Chem., Int. Ed. Engl. 33:1994;15-44.
12. Umezawa H., Aoyagi T., Suda H., Hamada M., Takeuchi T. J. Antibiot. 29:1976;97-99.
13. Ondetti M.A., Pluscec J., Weaver E.R., Williams N., Sabo E.F., Kocy O. Chemistry and Biology of Peptides. 1972;525-531 Ann Arbor Science Publishers, Ann Arbor.
14. Ondetti M.A., Engel S.L. J. Med. Chem. 18:1975;761-763.
15. Griffith O.W. Ann. Rev. Biochem. 55:1986;855-878.
16. Iizuka K., Kamijo T., Harada H., Akahane K., Kubota T., Umeyawa H., Kiso Y. J. Chem. Soc., Chem. Commun. 1989;1678-1680.
17. Rodríguez M., Fulcrand P., Laur J., Aumelas A., Bali J.P., Martínez J. J. Med. Chem. 32:1989;522-528.
18. Stachowiak K., Khosla M.C., Plucinska K., Khairallah P.A., Bumpus F.M. J. Med. Chem. 22:1979;1128-1130.
19. Cheng R.P., Gellman S.H., DeGrado W.F. Chem. Rev. 101:2001;3219-3232.
20. Palomo C., Oiarbide M., Bindi S. J. Org. Chem. 63:1998;2469-2474.
21. Drey C.N.C., Barnet G.C. Chemistry and Biochemistry of the Amino Acids. 1985;Chapman and Hall, London.
22. Juaristi E., Quintana D., Escalante J. Aldrichimica Acta. 27:1994;3-11.
23. Cole D.C. Tetrahedron. 50:1994;9517-9582.
24. Cardillo G., Tommasini C. Chem. Soc. Rev. 23:1996;117-128.
25. Juaristi E. Enantioselective Synthesis of β-amino Acids. 1997;Wiley-VCH, New York.
26. Bouteville G., Gelas-Mialhe Y., Vessiere R. Bull. Soc. Chim. Fr. 1971;3264-3270.
27. Wartski L., Wakselman C., Sierra-Escudero A. Bull. Soc. Chim. Fr. 1972;1478-1482.
28. Gelas-Mialhe Y., Touraud E., Vessiere R. Can. J. Chem. 60:1982;2830-2851.
29. Expert J., Gelas-Mialhe Y., Vessiere R. J. Heterocycl. Chem. 22:1985;1285-1289.
30. Pfau M. Bull. Soc. Chim. Fr. 1967;1117-1125.
31. D'Angelo J., Maddaluno J. J. Am. Chem. Soc. 108:1986;8112-8114.
32. Hawkins J.M., Lewis T.A. J. Org. Chem. 57:1992;2114-2121.
33. Davies S.G., Walters I.A.S. J. Chem. Soc., Perkin Trans.1. 1994;1129-1139.
34. Davies S.G., Ichihara O., Walters I.A.S. J. Chem. Soc., Perkin Trans. 1. 1994;1141-1147.
35. Davies S.G., Bunnage M.E., Goodwin C.J. J. Chem. Soc., Perkin Trans. 1. 1993;1375-1376.
36. Gasperi T., Loreto M.A., Tardella P.A., Gambacorta A. Tetrahedron Lett. 43:2002;3017-3020.
37. Lwowski W., Maricich T.J. J. Am. Chem. Soc. 87:1965;3630-3637.
38. Ciclosi M., Fava C., Galeazzi R., Orena M., Sepulveda-Arques J., Gonzalez-Rosende M.E. Heterocycles. 60:2003;1173-1183.
39. Francavilla M., Gasperi T., Loreto M.A., Tardella P.A., Bassetti M. Tetrahedron Lett. 43:2002;7913-7916.
40. Kuroda C., Kasahara T., Akiyama K., Amemiya T., Kunishima T., Kimura Y. Tetrahedron. 58:2002;4493-4504.
41. Hruby V.J., Al-Obeidi F., Kazmierski W. Biochem. J. 268:1990;249-262.
42. Heimgartner H. Angew. Chem., Int. Ed. Engl. 30:1991;238-265.
43. Rulev A., Maddaluno J. Eur. J. Chem. Org. 13:2001;2569-2576.
44. Fleming I., Terrett N. J. Organomet. Chem. 264:1984;99-118.
45. Davis F.A., Deng J., Zhang Y., Haltiwanger R.C. Tetrahedron. 58:2002;7135-7143.
46. Tanner D. Angew. Chem., Int. Ed. Engl. 33:1994;599-619.
47. McCoull W., Davis F.A. Synthesis. 10:2000;1347-1365.
48. +] (<1%), 180 (100%).