Application of 1,1,3,3-tetramethylguanidine in the reaction of amino acids with pantolactone

Tetrahedron Asymmetry

Volumn 15, Issue 15, 2004, Pages 2333-2338

  Wlostowski, Marek ^a   Rowicki, Tomasz ^a   Synoradzki, Ludwik ^a  

^a WARSAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

1,1,3,3 TETRAMETHYLGUANIDINE; AMINO ACID DERIVATIVE; GUANIDINE DERIVATIVE; PANTOLACTONE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL REACTION; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIZATION; REACTION ANALYSIS; SILYLATION;

EID: 4143096248     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.06.005     Document Type: Article

References (39)

1. Hubbard C.D., Wilson C.J., Caldin E.F. J. Am. Chem. Soc. 98:1976;1870-1875
2. Sasaki M., Sugimoto N., Osugi J. Chem. Lett. 1980;887-890
3. Kresge A.J., Powell M.F. J. Am. Chem. Soc. 103:1981;201-202
4. Caldin E.F., Mateo S., Warrick P. J. Am. Chem. Soc. 103:1981;202-204
5. Pruszyński P., Jarczewski A. J. Chem. Soc., Perkin Trans. 2. 1986;1117-1120
6. Galezowski W., Grześkowiak J., Jarczewski A. Can. J. Chem. 77:1999;1042-1049
7. Jarczewski A., Pruszyński P., Leffek K.T. Can. J. Chem. 61:1983;2029-2032
8. Hojatti M., Leffek K.T. Can. J. Chem. 62:1984;2653-2656
9. Hojatti M., Leffek K.T. Can. J. Chem. 64:1986;2365-2367
10. Leffek K.T., Pruszyński P. Can. J. Chem. 66:1988;1454-1458
11. Yang H.B., Taft R.W. J. Am. Chem. Soc. 93:1971;1310-1311
12. Joris L., Mitsky J., Taft R.W. J. Am. Chem. Soc. 94:1972;3438-3442
13. Nysted L.N., Burtner R.R. J. Org. Chem. 27:1962;3175-3177
14. Pollini G.P., Barco A., De Giuli G. Synthesis. 1972;44-45
15. Jaworski T., Kolodziejek W., Prejzner J., Wlostowski M. Pol. J. Chem. 55:1981;1321-1328
16. Hewson A.T., MacPherson D.T. Tetrahedron Lett. 24:1983;647-648
17. Kozikowski A.P., Xia Y., Reddy E.R., Tucmantel W., Hanin J., Tang X.C. J. Org. Chem. 56:1991;4636-4645
18. Simoni D., Invidiata F.P., Manfredini S., Ferroni R., Lampronti I., Robertini M., Pollini G.P. Tetrahedron Lett. 38:1997;2749-2752
19. Simoni D., Invidiata F.P., Manfredini S., Ferroni R., Lampronti I., Robertini M., Pollini G.P. Tetrahedron Lett. 39:1998;7615-7618
20. Simoni D., Rossi M., Rodanin R., Mazzali A., Baruchello R., Malaguti C., Roberti M., Invidiata F.P. Org. Lett. 2:2000;3765-3768
21. Wolfe S., Ducep J.-B., Tin K.-C., Lee S.-L. Can. J. Chem. 52:1974;3996-3999
22. Spry D.O. Tetrahedron Lett. 21:1980;1289-1292
23. Wolfe S., Shaw C.-C. Can. J. Chem. 60:1982;144-153
24. Papa A.J. J. Org. Chem. 31:1966;1426-1430
25. Sakai K., Anselme J.-P. J. Org. Chem. 36:1971;2387-2388
26. Dowd D., Wilk B.K., Wlostowski M. Synth. Commun. 23:1993;2323-2329
27. Ali A., Fahrenholz F., Weinstein B. Angew. Chem., Int. Ed. Engl. 11:1972;289
28. Kemp D.S., Wang S.-W., Rebek J. Jr., Mollan R.C., Banquer C., Subramanyam G. Tetrahedron. 30:1974;3955-3967
29. Kemp D.S., Wrobel S.J. Jr., Wang S.-W., Bernstein Z., Rebek J. Jr. Tetrahedron. 30:1974;3969-3980
30. Kemp D.S., Young E.C. Tetrahedron Lett. 35:1994;8315-8318
31. Luo J., Smith M.D., Lantrip D.A., Wang S., Fuchs P.L. J. Am. Chem. Soc. 119:1997;10004-10013
32. + in a similar process have been noticed for the reaction of various amino acids with 4,4-dimethyl-dihydro-furan-2,3-dione: Wlostowski, M.; Rowicki, T.; Grzeda, L.; Synoradzki, L. In preparation
33. Methods of GC and HPLC analysis will be the subject of a separate publication
34. Effenberger F., Eichorn J., Roos J. Tetahedron: Asymmetry. 6:1995;271-282
35. Williams R.J., Mitchell H.K., Weinstock H.H. Jr., Snell E.E. J. Am. Chem. Soc. 62:1940;1784-1785
36. Darke H.C., Lawson E.J. J. Am. Chem. Soc. 63:1941;2869-2871
37. Ford J.H. J. Am. Chem. Soc. 68:1946;1666-1668
38. Kagan F., Heinzelman R.V., Weisblat D.I., Greiner W. J. Am. Chem. Soc. 79:1957;3545-3549
39. Delmar, G.; Kubela, R. Patent GB 1,183,387, C.A. 1970, 72:132087e