Crystallization-induced asymmetric transformation. Application to conjugate addition of benzylamine to amides of benzoylacrylic acid

Tetrahedron Letters

Volumn 45, Issue 24, 2004, Pages 4755-4758

  Jakubec, Pavol ^a   Berkeš, Dušan ^a   Považanec, František ^a  

^a SLOVAK UNIVERSITY OF TECHNOLOGY   (Slovakia)

Author keywords

Asymmetric transformation; Crystallization induced; Dipeptide; Homophenylalanine

Indexed keywords

ACRYLIC ACID DERIVATIVE; AMIDE; BENZYLAMINE DERIVATIVE; DIPEPTIDE DERIVATIVE; PHENYLALANINE;

ARTICLE; CRYSTALLIZATION; DIASTEREOISOMER; ENANTIOMER; STEREOCHEMISTRY; SYNTHESIS;

EID: 2442691353     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.04.066     Document Type: Article

References (20)

1. Eliel E.L., Wilen S.H., Mander L.N. Stereochemistry of Organic Compounds. 1994;John Wiley & Sons, New York. pp 364-374
2. Caddick S., Jenkins K. Chem. Soc. Rev. 1996;447-456
3. Vedejs E., Chapman R.W., Lin S., Müller M., Powell D.R. J. Am. Chem. Soc. 122:2000;3047-3052
4. Yamaha M., Nagashima N., Hasegawa J., Takahashi S. Tetrahedron Lett. 39:1998;9019-9022
5. Kolarovic A., Berkes D., Baran P., Povazanec F. Tetrahedron Lett. 42:2001;2579-2582
6. Berkes D., Lopuch J., Proksa B., Povazanec F. Chem. Pap. 57:2003;349-353
7. Berkes D., Kolarovic A., Povazanec F. Tetrahedron Lett. 41:2000;5257-5260
8. Chapman K.T., Wales J., Sahoo S.P., Niedzwiecki L.M., Izqulerdo-Martin M., Chang B.C., Harrison R.K., Stein R.L., Hangmann W.K. Bioorg. Med. Chem. Lett. 6:1996;329-332
9. Rockwell A., Melden M., Copeland R.A., Hardman K., Decicco C.P., DeGrado W.F. J. Am. Chem. Soc. 118:1996;10337-10338
10. Renau T.E., Léger R., Filonova L., Flamme E.M., Wang M., Yen R., Madsen D., Griffith D., Chamberland S., Dudley M.N., Lee V.J., Lomovskaya O., Watkins W.J., Ohta T., Nakayama K., Ishida Y. Bioorg. Med. Chem. Lett. 13:2003;2755-2758
11. Renau T., Léger R., Flamme E.M., She M.W., Gannon C.L., Mathias K.M., Lomovskaya O., Chamberland S., Lee V.J., Ohta T., Nakayama K., Ishida Y. Bioorg. Med. Chem. Lett. 11:2001;663-667
12. Berrée F., Chang K., Cobas A., Rapoport H. J. Org. Chem. 61:1996;715-721
13. Pinto I.L., Jarvest R.L., Clarke B., Dabrowski C.E., Fenwick A., Gorczyca M.M., Jennings L.J., Lavery P., Sternberg E.J., Tew D.G., West A. Bioorg. Med. Chem. Lett. 9:1999;449-452
14. Anderson G.W., Zimmerman J.E., Callahan F.M. J. Am. Chem. Soc. 86:1964;1839-1842
15. 6 ): 25.41 (C-3, C-4); 124.74; 128.97; 134.30; 135.45 (Ph, C-2′); 142.13 (C-3′); 161.06 (C-1′); 169.90 (C-2, 5); 188.46 (C-4′))
16. 3): 37.3 (C-3); 53.7 (C-2); 127.3; 128.7; 128.8; 129.0; 129.3; 133.9; 134.0; 134.6; 135.5; 134.5 (C-Arom, C-2′, C-3′); 164.5 (C-1′); 174.2 (C-1); 190.0 (C-4′))
17. Harada K., Matsumoto K. J. Org. Chem. 31:1966;2985-2990
18. 2NH); 54.7 (C-2); 56.2 (C-2′); 127.3; 128.9; 129.0; 129.6; 130.1; 131.1; 131.3; 134.6; 136.3; 137.9 (C-Arom); 167.5 (C-1′); 172.5 (C-1); 196.9 (C-4′))
19. 6 /DCl): 30.4 (C-4′); 33.7 (C-3); 36.6 (C-3′); 52.2 (C-2′); 54.5 (C-2); 126.6, 127.1, 128.7, 128.9, 129.0, 129.6, 137.7, 141.4 (C-Arom); 168.9 (C-1′); 172.9 (C-1))
20. Bodansky M., Bodansky A. The Practice of Peptide Synthesis. 1994;Springer, Berlin Heidelberg. p 209