Multicomponent solution phase synthesis of dehydroamino acid derivatives based on the Passerini reaction

Tetrahedron Letters

Volumn 39, Issue 39, 1998, Pages 7031-7034

  Kim, Sang Woong ^a,b   Bauer, Shawn M ^a   Armstrong, Robert W ^a,c  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b LG Chemical Ltd   (South Korea)

^c AMGEN INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE;

AMINO ACID ANALYSIS; AMINO ACID SYNTHESIS; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; POLYMERIZATION;

EID: 0032563979     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01522-6     Document Type: Article

References (25)

1. 3. See leading reviews (a) Hermkens, P.H.H.; Ottenheijm, H.C.J.; Rees, D. Tetrahedron Lett. 1997, 53, 5643.
2. (b) Lam, K.S.; Lebl, M.; Krchnak, V. Chem. Rev. 1997, 97, 411.
3. (c) Nefzi, A.; Ostresh, J.M.; Houghten, R.A. Chem. Rev. 1997, 97, 449.
4. (d) Armstrong, R.W.; Combs, A.P.; Tempest, P.A.; Brown, S.D.; Keating, T.A. Acc. Chem. Res. 1996, 29, 123.
5. (e) Hermkens, P.H.H.; Ottenheijm, H.C.J.; Rees, D. Tetrahedron Lett. 1996, 52, 4527.
6. (f) Thompson, L.A.; Ellman, J.A. Chem. Rev. 1996, 96, 555.
7. (g) Fennir, H. Current Medicinal Chem. 1996, 3, 343.
8. (h) Williard, X.; Pop, I.; Bourel, L.; Horvath, D.; Baudelle, R.; Melnyk, P.; Deprez, B.; Tartar, A. Eur. J. Med. Chem. 1996, 31, 87
9. (i) Terrett, N.K.; Gardner, M.; Gordon, D.W.; Kobylecki, R.J.; Steele, J. Tetrahedron 1995, 51, 8135.
10. (j) Gallop, M.A.; Barrett, R.W.; Dower, W.J.; Fodor, S.P.A.; Gordon, E.M. J. Med. Chem. 1994, 37, 1233.
11. (k) Gordon, E.M.; Barrett, R.W.; Dower, W.J.; Fodor, S.P.A.; Gallop, M.A. J. Med. Chem. 1994, 37, 1385.
12. (l) Desai, M.C.; Zuckerman, R.N.; Moos, W.H. Drug Development Research 1994, 33, 174.
13. 4. (a) Boger, D.L.; Tarby, C.M.; Myers, P.L.; Caporale, L.H. J. Am. Chem. Soc. 1996, 118, 2109.
14. (b) Cheng, S.; Comer, D.D.; Williams, J.P.; Myers, P.L.; Boger, D.L. J. Am. Chem. Soc. 1996, 118, 2567.
15. (c) Cheng, S.; Tarby, C.M.; Comer, D.D.; Williams, J.P.; Caporale, L.H.; Myers, P.L.; Boger, D.L. Bioorganic & Medicinal Chemistry, 4, 717.
16. (d) Pirrung, M.C.; Chen, J. J. Am. Chem. Soc. 1995, 117, 1240.
17. (e) Smith, P.W.; Lai, J.Y.Q.; Whittington, A.R.; Cox, B.; Houston, J.G.; Stylli, C.H.; Banks, M.N.; Tiller, P.R. Bioorg. Med. Chem. Lett. 1994, 4, 2821.
18. (f) Carell, T.; Wintner, E.A.; Bashir-Hashemi, A.; Rebek, J., Jr. Angew Chem. Int. Ed. Engl. 1994, 33, 2059.
19. 5. (a) Wipf, P.; Cunningham, A. Tetrahedron Lett. 1995, 36, 7819.
20. (b) Ugi, I.; Domling, A.; Horl, W. Endeavour, 1994, 18, 115.
21. (c) Studer, A.; Jeger, P.; Wipf, P.; Curran, D.P. J. Org. Chem. 1997, 62, 2917.
22. 6. Armstrong, R.W.; Salvati, M.E.; Nguyen, M. J. Am. Chem. Soc. 1992, 114, 3145.
23. 7. (a) Armstrong, R. W.; Moran, E. J. J. Am. Chem. Soc. 1992, 114, 371.
24. (b) Moran, E.J.; Tellew, J.E.; Zhao, Z.; Armstrong, R.W. J. Org. Chem. 1993, 58, 7848.
25. 2, RT, 8-12h.