A facile synthesis of ethyl 2-acetamido-4-methylenehex-5-enoate, a versatile Diels-Alder synthon for the parallel synthesis of novel α-amino acid derivatives

Synthesis

Volumn , Issue 1, 2007, Pages 113-117

  Chen, Rui ^a   Lee, Victor ^a   Adlington, Robert M ^a   Baldwin, Jack E ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

Amino acid; Coupling; Diels Alder; Diene; Palladium

Indexed keywords

COUPLING; DIELS-ALDER SYNTHON; DIENE;

AMINO ACIDS; DERIVATIVES; PALLADIUM; REACTION KINETICS; SYNTHESIS (CHEMICAL);

AROMATIC COMPOUNDS;

ACETAMIDE DERIVATIVE; AMINO ACID DERIVATIVE; ETHYL 2 ACETAMIDO 4 METHYLENEHEX 5 ENOATE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DIELS ALDER REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 33947508615     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-958929     Document Type: Article

References (32)

1. (a) Williams, R. M. In Synthesis of Optically Active α-Amino Acids; Baldwin, J. E., Ed.; Pergamon Press: Oxford, 1989.
2. (b) Williams, R. M.; Hendrix, J. A. Chem. Rev. 1992, 92, 889.
3. (c) Duthaler, R. O. Tetrahedron 1994, 50, 1539.
4. (d) Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2708.
5. (e) Cativiela, C.; Diaz-de-Villegas, M. D. Tetrahedron: Asymmetry 1998, 9, 3517.
6. (f) Maruoka, K.; Ooi, T. Chem. Rev. 2003, 103, 3013.
7. See, for example (a) Moloney, M. G. Nat. Prod. Rep. 1998, 15, 205.
8. (b) Moloney, M. G. Nat. Prod. Rep. 1999, 16, 485.
9. (c) Moloney, M. G. Nat. Prod. Rep. 2002, 19, 597.
10. (a) Adlington, R. M.; Baldwin, J. E.; Catterick, D.; Pritchard, G. J. Chem. Commun. 1997, 1757.
11. (b) Adlington, R. M.; Baldwin, J. E.; Catterick, D.; Pritchard, G. J. J. Chem. Soc., Perkin Trans. 1 1999, 855.
12. (c) Adlington, R. M.; Baldwin, J. E.; Catterick, D.; Pritchard, G. J. J. Chem. Soc., Perkin Trans. 1 2000, 299.
13. (d) Adlington, R. M.; Baldwin, J. E.; Catterick, D.; Pritchard, G. J.; Tang, L. T. J. Chem. Soc, Perkin Trans. 1 2000, 303.
14. (e) Adlington, R. M.; Baldwin, J. E.; Catterick, D.; Pritchard, G. J.; Tang, L. T. J. Chem. Soc, Perkin Trans. 1 2000, 2311.
15. (f) Adlington, R. M.; Baldwin, J. E.; Catterick, D.; Pritchard, G. J. J. Chem. Soc., Perkin Trans. 1 2001, 668.
16. (a) Kotha, S.; Brahmachary, E.; Sreenivasachary, N. Tetrahedron Lett. 1998, 39, 4095.
17. (b) Kotha, S.; Sreenivasachary, N.; Brahmachary, E. Eur. J. Org. Chem. 2001, 787.
18. (c) Kotha, S.; Halder, S.; Brahmachary, E. Tetrahedron 2002, 58, 9203.
19. (d) Kotha, S. Acc. Chem. Res. 2003, 36, 342.
20. (e) Kotha, S.; Ghosh, A. K. Tetrahedron Lett. 2004, 45, 2931.
21. (f) Kotha, S.; Ghosh, A. K. Tetrahedron 2004, 60, 10833.
22. (g) Kotha, S.; Ghosh, A. K. Synthesis 2004, 558.
23. (a) Efskind, J.; Römming, C.; Undheim, K. J. Chem. Soc., Perkin Trans. 1 2001, 2697.
24. (b) Møller, B. S.; Undheim, K. Synth. Commun. 2003, 33, 4209.
25. Leanna, M. R.; Morton, H. E. Tetrahedron Lett. 1993, 34, 4485.
26. Trost, B. M. Science 1991, 254, 1471.
27. Crisp, G. T.; Geauber, M. G. Tetrahedron Lett. 1995, 36, 3389.
28. Denmark, S. E.; Butler, C. R. Org. Lett. 2006, 8, 63.
29. (a) Krapcho, A. P. Synthesis 1982, 805.
30. (b) Krapcho, A. P. Synthesis 1982, 893.
31. (a) Cookson, R. C.; Gilani, S. S. H.; Stevens, I. D. R. J. Chem. Soc. C 1967, 1905.
32. (b) Brown, P. A.; Bonnert, R. V.; Jenkins, P. R.; Lawrence, N. J.; Selim, M. R. J. Chem. Soc., Perkin Trans. 1 1991, 1839.