Stereoselective synthesis of heterosubstituted aziridines and their functionalization

Tetrahedron

Volumn 60, Issue 5, 2004, Pages 1175-1182

  De Vitis, Luisella ^a   Florio, Saverio ^b   Granito, Catia ^a   Ronzini, Ludovico ^a   Troisi, Luigino ^a   Capriati, Vito ^b   Luisi, Renzo ^b   Pilati, Tullio ^c  

^a UNIVERSITY OF SALENTO   (Italy)

^b UNIVERSITY OF BARI   (Italy)

^c UNIVERSITY OF MILAN   (Italy)

Author keywords

Aziridinyl anion; Heterosubstituted aziridines; Nucleophilic addition

Indexed keywords

2 [1 (2 METHOXY 1 PHENYLETHYL) 2 METHYL 3 PHENYLAZIRIDIN 2 YL] 4 METHYLTHIAZOLE; 2 [1 (2 METHOXY 1 PHENYLETHYL) 2 METHYL 3 PHENYLAZIRIDIN 2 YL] 4,4 DIMETHYL 4,5 DIHYDROOXAZOLE; 2 [1 (2 METHOXY 1 PHENYLETHYL) 2 METHYL 3 PHENYLAZIRIDIN 2 YL]BENZOTHIAZOLE; 2 [1 (2 METHOXY 1 PHENYLETHYL) 3 PHENYLAZIRIDIN 2 YL] 4 METHYLTHIAZOLE; 2 [1 (2 METHOXY 1 PHENYLETHYL) 3 PHENYLAZIRIDIN 2 YL] 4,4 DIMETHYL 4,5 DIHYDROOXAZOLE; 2 [1 (2 METHOXY 1 PHENYLETHYL) 3 PHENYLAZIRIDIN 2 YL]BENZOTHIAZOLE; 2 [1 (2 METHOXY 1 PHENYLETHYL) 3 PHENYLAZIRIDIN 2 YL]PYRIDINE; 2 [2 DEUTERO 1 (2 METHOXY 1 PHENYLETHYL) 3 PHENYLAZIRIDIN 2 YL] 4 METHYLTHIAZOLE; 2 [2 DEUTERO 3 PHENYL 1 (1 PHENYLETHYL)AZIRIDIN 2 YL] 4 METHYLTHIAZOLE; 2 [2 METHYL 3 PHENYL 1 (1 PHENYLETHYL)AZIRIDIN 2 YL] 4,4 DIMETHYL 4,5 DIHYDROOXAZOLE; 2 [3 PHENYL 1 (1 PHENYLETHYL)AZIRIDIN 2 YL] 4 METHYLTHIAZOLE; 4 [1 (2 METHOXY 1 PHENYLETHYL) 3 PHENYLAZIRIDIN 2 YL]PYRIDINE; AZIRIDINE DERIVATIVE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; LITHIATION; PRIORITY JOURNAL; PROTON TRANSPORT; STEREOCHEMISTRY; SYNTHESIS;

EID: 0348230552     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.11.056     Document Type: Article

References (41)

1. Baldwin J.E., Farthing C.N., Russel A.T., Schofield C.J., Spivey A.C. Tetrahedron Lett. 37:1996;3761-3764.
2. Garner P., Dogan O., Pillai S. Tetrahedron. 35:1994;1653-1656.
3. Deyrup J.A. Hassner A. The chemistry of heterocyclic compounds. Vol. 42:1983;1-124 Wiley, New York.
4. Pearson W.H., Lion B.W., Bergmeier S.C. Padwa A. Comprehensive heterocyclic chemistry II. Vol. 1A:1996;1-60 Pergamon, Oxford.
5. Rai K.M.L., Hassner A. Padwa A. Comprehensive heterocyclic chemistry II. Vol. 1A:1996;61-96 Pergamon, Oxford.
6. Contrill A.A., Osborn H.M.I., Sweeney J.B. Tetrahedron. 54:1998;2181-2208.
7. Tanner D. Angew. Chem. Int. Ed. Engl. 33:1994;599-619.
8. Osborn H.M.I., Sweeney J.B. Tetrahedron: Asymmetry. 8:(11):1997;1693- 1715.
9. Mc Coull W., Davis F.A. Synthesis. (10):2000;1347-1365.
10. Satoh T. Chem. Rev. 96:1996;3303-3325.
11. Vedejs E., Moss W.O. J. Am. Chem. Soc. 115:1993;1607-1608.
12. Vedejs E., Kendall J.T. J. Am. Chem. Soc. 119:1997;6941-6942.
13. Alezra V., Bonin M., Micouin L., Policar C., Husson H.-P. Eur. J. Org. Chem. 2001;2589-2594.
14. Reutrakul V., Prapansiri V., Panyachotipun C. Tetrahedron Lett. 25:1984;1949.
15. Seebach D., Haner R. Chem. Lett. 1987;49.
16. Haner R., Olano B., Seebach D. Helv. Chim. Acta. 70:1987;1676.
17. Florio S., Troisi L., Capriati V. J. Org. Chem. 60:1995;2279-2282.
18. Florio S., Troisi L., Capriati V. Tetrahedron Lett. 39:1998;7951-7954.
19. Florio S., Troisi L., Capriati V., Ingrosso G. Tetrahedron Lett. 40:1999;6101-6104.
20. Bona F., De Vitis L., Florio S., Ronzini L., Troisi L. Tetrahedron. 59:2003;1381-1387. and ref. therein.
21. Corey E.J., Boger D.L. Tetrahedron Lett. 1:1978;13-16.
22. Florio S., Capriati V., Luisi R. Tetrahedron Lett. 37:1996;4781-4784.
23. Dondoni A. Scheffold R. Modern synthetic methods. 1992;377-473 Helvetica Chimica Acta, Basel, Switzerland.
24. Dondoni A., Perrone D. Aldrichim. Acta. 30:1997;35-46.
25. Luisi R., Capriati V., Florio S., Ranaldo R. Tetrahedron Lett. 44:2003;2677-2681.
26. Wartski L. Bull. Soc. Chim. Fr. 1975;1663.
27. Alvernhe G., Laurent A. Bull. Soc. Chim. Fr. 8-9:1970;3003-3010.
28. Kingsbury C.A., Durham D.L., Hutton R. J. Org. Chem. 43:1978;4696-4700.
29. CCDC 212745 contain the supplementary crystallographic data (excluding structure factors) for compound (+)-3b . These data can be obtained free of charge via www.ccdc.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44-1223-336-033; or deposit@ccdc.cam.ac.uk ).
30. Yonezawa T., Morishima I. J. Mol. Spectry. 27:1968;210.
31. CH=162.7 Hz) in the case of compound (+)-3b.
32. All calculations and graphical representations were performed by SPARTAN, Version 02, Wavefunction, Inc., Irvine, CA, USA, 2002.
33. Suffert J. J. Org. Chem. 54:1989;509-512.
34. Chikashita H., Ikegami S., Okumura T., Itoh K. Synthesis. 5:1986;375-377.
35. Zubarovskii V.M. Zhr. Obsch. Khim. 24:1954;1664. Chem Abstr. 1955, 49, 13223.
36. Altamura M., Perrotta E. J. Org. Chem. 58:1993;272-274.
37. Florio S., Granito C., Ingrosso G., Troisi L. Eur. J. Org. Chem. 2000;3465-3472. and ref. therein.
38. Capriati V., Florio S., Ingrosso G., Granito C., Troisi L. Eur. J. Org. Chem. 2000;478-484. and references therein cited.
39. Taguchi K., Westheimer F.H. J. Org. Chem. 36:1971;1570-1572.
40. De Kimpe N., De Cock W., Stevens C. Tetrahedron. 48:1992;2739-2760.
41. Smith A.B., Yager K.M., Taylor C.M. J. Am. Chem. Soc. 117:1995;10879-10888.