Synthesis and photooxygenation of homochiral 2-methylpyrrole derivatives of chiral amino alcohols: Simple, selective access to chiral bicyclic lactams

Tetrahedron Asymmetry

Volumn 15, Issue 2, 2004, Pages 259-265

  Aydogan, Feray ^a,b   Demir, Ayhan S ^a  

^a MIDDLE EAST TECHNICAL UNIVERSITY   (Turkey)

^b YILDIZ TECHNICAL UNIVERSITY   (Turkey)

Author keywords

[No Author keywords available]

Indexed keywords

5 CHLORO 3 PENTEN 2 ONE; AMINOALCOHOL; LACTAM DERIVATIVE; PENTANE; PYRROLE DERIVATIVE; PYRROLOOXAZOLONE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DIASTEREOISOMER; DRUG SYNTHESIS; PHOTOOXIDATION; PHOTOSYNTHESIS; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; TRANS ISOMER;

EID: 0347600477     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.11.011     Document Type: Article

References (39)

1. Scharf H., Esser P. Angew. Chem., Int. Ed. Engl. 33:1994;2009.
2. Li H., De Lucca I., Drummond S., Boswell G.A. Heterocycles. 43:1996;937.
3. Balci M. Chem. Rev. 81:1981;91.
4. Wasserman H.H., Lipshutz B.H. Wasserman H.H., Murray R.W. Singlet Oxygen. 1979;Academic, New York.
5. Wasserman H.H., De Simone R.W., Boger D.L., Baldino C.M. J. Am. Chem. Soc. 115:1993;8457.
6. Wasserman H.H., Frechette R., Rotello V.M. Tetrahedron Lett. 32:1991;7571.
7. Li H.-Y., Drummond S., De Lucca I., Boswell G.A. Tetrahedron. 52:1996;11153.
8. Wasserman H.H., Wolff M.S., Stiller K., Saito I., Pickett J.E. Tetrahedron. (suppl. 9):1981;191.
9. Zhang X., Khan S.I., Foote C.S. J. Org. Chem. 58:1993;7839.
10. Wasserman H.H., Petersen A.K., Xia M., Wang J. Tetrahedron Lett. 40:1999;7587.
11. Wasserman H.H., Xia M., Wang J., Petersen A.K., Jorgensen M. Tetrahedron Lett. 40:1999;6145.
12. Franck R.W., Auerbach J. J. Org. Chem. 36:1971;31.
13. Lightner D.A., Bisacchi G.S., Norris R.D. J. Am. Chem. Soc. 98:1976;802.
14. Ligtner D.A., Quistad G.B. Angew. Chem., Int. Ed. Engl. 11:1972;215.
15. Demir A.S., Akhmedov I.M., Şeşenoglu Ö., Alptürk O., Apaydin S., Gerçek Z., Ibrahimzade N. J. Chem. Soc., Perkin Trans. 1. 2001;1162.
16. Demir A.S., Akhmedov I.M., Tanyeli C., Gerçek Z., Gadzhili R.A. Tetrahedron: Asymmetry. 5:1997;753.
17. Demir A.S., Aydogan F., Akhmedov I.M. Tetrahedron: Asymmetry. 13:2002;601.
18. Romo D., Romine J.L., Midura W., Meyers A.I. Tetrahedron. 46:1990;4951.
19. Meyers A.I., Fleming S.A. J. Am. Chem. Soc. 108:1986;306.
20. Meyers A.I., Garland R.J. J. Am. Chem. Soc. 106:1984;1146.
21. Meyers A.I., Wanner K.T. Tetrahedron Lett. 26:1985;2047.
22. Meyers A.I., Busacca C.A. Tetrahedron Lett. 30:1989;6973.
23. Meyers A.I., Busacca C.A. Tetrahedron Lett. 30:1989;6977.
24. Busacca C.A., Meyers A.I. J. Chem. Soc., Perkin Trans. 1. 1991;2299.
25. Meyers A.I., Berney D. J. Org. Chem. 54:1989;4673.
26. Meyers A.I., Sturgess M.A. Tetrahedron Lett. 30:1989;1741.
27. Meyers A.I., Bienz S. J. Org. Chem. 55:1990;791.
28. Brengel G.P., Meyers A.I. J. Org. Chem. 61:1996;3230.
29. Fray A.H., Meyers A.I. Tetrahedron Lett. 33:1992;3575.
30. Meyers A.I., Romo D. Tetrahedron Lett. 30:1989;1745.
31. Meyers A.I., Romine J.L., Fleming S.A. J. Am. Chem. Soc. 110:1988;7245.
32. Faltz H., Bohrisch J., Wohlauf W., Patzel M., Jones P.G., Liebscher J. Tetrahedron. 52:1996;9035.
33. Fray A.H., Meyers A.I. J. Org. Chem. 61:1996;3362.
34. Armstrong D.W., He L., Yu T., Lee J.T., Liu Y. Tetrahedron: Asymmetry. 10:1999;37.
35. Meyers A.I., Lefker B.A., Sowin T.J., Westrum L.J. J. Org. Chem. 54:1989;4243.
36. Meyers A.I., Lefker B.A. Tetrahedron. 43:1987;5663.
37. Foote C.S., Wexler W.A., Higgins R. J. Am. Chem. Soc. 90:1968;975.
38. Kearns D.R., Radlick P.H., Chambers R. J. Am. Chem. Soc. 89:1967;5456.
39. Wasserman H.H., Scheffer S.R. J. Am. Chem. Soc. 89:1967;3073.