α,β-Didehydroamino acid derivatives with an isoxazolyl or a pyrazolyl moiety: The effect of substituents and reaction conditions on their stereoselective formation from 2H-pyran-2-ones

Journal of the Chemical Society. Perkin Transactions 1

Volumn 2, Issue 5, 2002, Pages 675-681

  Vraniar, Lidija ^a   Meden, Anton ^a   Polanc, Slovenko ^a   Koevar, Marijan ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLATION; CATALYSTS; CHEMICAL BONDS; CHROMATOGRAPHY; CRYSTALLIZATION; DATA ACQUISITION; DERIVATIVES; ELECTRONS; ETHANOL; HYDRAZINE; HYDROGENATION; ISOMERS; NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); THERMODYNAMIC STABILITY;

CHEMICAL SHIFTS;

AMINO ACIDS;

EID: 0036006427     PISSN: 14727781     EISSN: 13645463     Source Type: Journal    
DOI: 10.1039/b107624h     Document Type: Article

References (26)

1. U. Schmidt, A. Lieberknecht, J. Wild Synthesis 1988, 159.
2. R.O. Duthaler Tetrahedron 1994, 50, 1539.
3. R. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon Press, Oxford, 1989, pp. 230–256.
4. R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994, pp. 16–94.
5. M. Nógrádi, Stereoselective Synthesis, VCH, Weinheim, 2nd edn., 1995, pp. 45–65.
6. U. Nagel, J. Albrecht Top. Catal. 1998, 5, 3.
7. M.J. Burk Acc. Chem. Res. 2000, 33, 363.
8. A.V. Komarov, A. Börner Angew. Chem., Int. Ed. 2001, 40, 1197.
9. A.N. Bowler, A. Dinsmore, P.M. Doyle, D.W. Young J. Chem. Soc., Perkin Trans. 1 1997, 1297.
10. T.N. Johansen, B. Ebert, H. Bräuner-Osborne, M. Didriksen, I.T. Christensen, K.K. Søby, U. Madsen, P. Krogsgaard-Larsen, L. Brehm J. Med. Chem. 1998, 41, 930.
11. E. Falch, L. Brehm, I. Mikkelsen, T.N. Johansen, N. Skjærbæk, B. Nielsen, T.B. Stensbøl, B. Ebert, P. Krogsgaard-Larsen J. Med. Chem. 1998, 41, 2513.
12. R.M. Adlington, J.E. Baldwin, D. Catterick, G.J. Pritchard, L.T. Tang J. Chem. Soc., Perkin Trans. 1 2000, 2311.
13. S.B. Vogensen, H.S. Jensen, T.B. Stensbøl, K. Frydenvang, B. Bang-Andersen, T.N. Johansen, J. Egebjerg, P. Krogsgaard-Larsen Chirality 2000, 12, 705.
14. U. Madsen, H. Bräuner-Osborne, K. Frydenvang, L. Hvene, T.N. Johansen, B. Nielsen, C. Sanchez, T.B. Stensbøl, F. Bischoff, P. Krogsgaard-Larsen J. Med. Chem. 2001, 44, 1051.
15. P.M.T. Ferreira, H.L.S. Maia, L.S. Monteiro, J. Sacramento Tetrahedron Lett. 2000, 41, 7437.
16. P. Trebe, S. Polanc, M. Koevar, T. olmajer, S. Goli Grdadolnik Tetrahedron 1997, 53, 1383.
17. L. Vraniar, S. Polanc, M. Koevar Tetrahedron 1999, 55, 271.
18. S.A. Lang, Jr. and Y.-I. Lin, in Comprehensive Heterocyclic Chemistry, ed. A. R. Katritzky and C. W. Rees, Pergamon Press, Oxford, 1984, vol. 6, pp. 1–130.
19. M. Sutharchanadevi and R. Murugan, in Comprehensive Heterocyclic Chemistry II, ed. A. R. Katritzky, C. W. Rees and E. F. V. Scriven, Pergamon Press, Oxford, 1996, vol. 3, pp. 221–260.
20. J. Elguero, in Comprehensive Heterocyclic Chemistry, ed. A. R. Katritzky and C. W. Rees, Pergamon Press, Oxford, 1984, vol. 5, pp. 167–343.
21. J. Elguero, in Comprehensive Heterocyclic Chemistry II, ed. A. R. Katritzky, C. W. Rees and E. F. V. Scriven, Pergamon Press, Oxford, 1996, vol. 3, pp. 1–75.
22. K. Makino, H.S. Kim, Y. Kurasawa J Heterocycl. Chem. 1999, 36, 321.
23. V. Kepe, M. Koevar, S. Polanc, B. Verek, M. Tiler Tetrahedron 1990, 46, 2081.
24. M. Begtrup, G. Boyer, P. Cabildo, C. Cativiela, R.M. Claramunt, J. Elguero, J.I. García, C. Toiron, P. Vedsø Magn. Reson. Chem. 1993, 31, 107.
25. U. Schmidt, A. Lieberknecht Angew. Chem. 1983, 95, 575.
26. N. Takahayashi J. Pharm. Soc. Jpn. 1956, 76, 765 Chem. Abstr. 1957, 51, 1192d.