Enantioselective synthesis of γ-functionalized α-dehydroamino esters

Synthesis

Volumn , Issue 24, 2007, Pages 3923-3925

  Palacios, Francisco ^a   Vicario, Javier ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

Amino acids; Asymmetric catalysis; Imines; Michael addition; Organometallics

Indexed keywords

ASYMMETRIC CATALYSIS; IMINES; MICHAEL ADDITION;

ADDITION REACTIONS; AMINO ACIDS; CATALYSIS; COPPER; ENANTIOSELECTIVITY; ESTERS; SYNTHESIS (CHEMICAL);

ORGANOMETALLICS;

ALPHA DEHYDROAMINO ESTER DERIVATIVE; BETA,GAMMA ALPHA IMINO ESTER DERIVATIVE; COPPER; DIETHYLZINC; ESTER DERIVATIVE; PHOSPHORAMIDOUS ACID; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; ENANTIOSELECTIVITY; MICHAEL ADDITION; SYNTHESIS;

EID: 37549016725     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-983840     Document Type: Article

References (35)

1. Some recent contributions to hydrogenation of α-dehydroamino acids: (a) Zhang, W.; Zhang, X. J. Org. Chem. 2007, 72, 1020.
2. (b) Hu, X.-P.; Huang, J.-D.; Zeng, Q.-H.; Zheng, Z. Chem. Commun. 2006, 293.
3. (c) Hoen, R.; Van den Berg, M.; Bernsmann, H.; Minnaard, A. J.; De Vries, J. G.; Feringa, B. L. Org. Lett. 2004, 6, 1433.
4. (a) Cerić, H.; Kovačević, M.; Šindler-Kulyk, M. Tetrahedron 2000, 56, 3985.
5. (b) Hou, D.; Mas, J. L.; Chan, T. M.; Wong, Y. S.; Steinman, M.; McPhail, A. T. Bioorg. Med. Chem. Lett. 1993, 3, 2171.
6. (c) Farina, V.; Hauck, S. I.; Walker, D. G. Synlett 1992, 76.
7. (a) El Ashry, E. S. H.; Ramadan, E. S.; Abdel Hamid, H.; Hagar, M. Lett. Org. Chem. 2005, 2, 415.
8. (b) Cvetovich, R. J.; Pipik, B.; Hartner, F. W.; Grabowski, E. J. J. Tetrahedron Lett. 2003, 44, 5867.
9. (c) Nagasaki, A.; Adachi, Y.; Yonezawa, Y.; Shin, C.-G. Heterocycles 2003, 60, 321.
10. (d) Arnold, Z. Synthesis 1990, 39.
11. (e) Breslow, R.; Canary, J. W.; Varney, M.; Waddell, S. T.; Yang, D. J. Am. Chem. Soc. 1990, 112, 5212.
12. For reviews about α-dehydroamino acid compounds, see: (a) RajanBabu, T. V.; Yan, Y. Y.; Shin, S. Curr. Org. Chem. 2003, 7, 1759.
13. (b) Drexler, H. J.; You, J.; Zhang, S.; Fisher, C.; Bauman, W.; Spannenberg, A.; Heller, D. T. Org. Process Res. Dev. 2003, 7, 355.
14. (c) Brunner, H. Curr. Org. Chem. 2002, 6, 441.
15. (d) Schmidt, U.; Lieberknecht, A.; Wild, J. Synthesis 1988, 159.
16. (a) Broda, M. A.; Siodłak, D.; Rzeszotarska, B. J. Pept. Sci. 2005, 11, 546.
17. (b) Mathur, P.; Ramakumar, S.; Chauhan, V. S. Biopolymers 2004, 76, 150.
18. (c) Vijayaraghavan, R.; Kumar, P.; Dey, S.; Singh, T. P. J. Pept. Res. 2003, 62, 63.
19. (a) Chen, D.; Guo, L.; Liu, J.; Kirtane, S.; Cannon, J. F.; Li, G. Org. Lett. 2005, 7, 921.
20. (b) Sai, H.; Ogiku, T.; Ohmizu, H. Synthesis 2003, 201.
21. (c) Ferreira, P. M. T.; Maia, H. L. S.; Monteiro, L. S.; Sacramento, J. J. Chem. Soc., Perkin Trans. 1 1999, 3697.
22. (d) Stohlmeyer, M. M.; Tanaka, H.; Wandless, T. J. J. Am. Chem. Soc. 1999, 121, 6100.
23. (e) Ferreira, P. M. T.; Maia, H. L. S.; Montiro, L. S. Tetrahedron Lett. 1998, 39, 9575.
24. Groundwater, P. W.; Sharif, T.; Arany, A.; Hibbs, D. E.; Hursthouse, M. B.; Nyerges, M. Tetrahedron Lett. 1998, 39, 1433.
25. Davis, F. A.; Liu, H.; Liang, C.-H.; Venkat Reddy, G.; Zhang, Y.; Fang, T.; Titus, D. D. J. Org. Chem. 1999, 64, 8929.
26. Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595.
27. Schmidt, U.; Griesser, H.; Leitenberger, V.; Lieberknecht, A.; Mangold, R.; Meyer, R.; Riedl, B. Synthesis 1992, 487.
28. (a) Palacios, F.; Vicario, J.; Maliszewska, A.; Aparicio, D. J. Org. Chem. 2007, 72, 2682.
29. (b) Palacios, F.; Vicario, J.; Aparicio, D. J. Org. Chem. 2006, 71, 7690.
30. (c) Palacios, F.; Alonso, C.; Rubiales, G.; Villegas, M. Tetrahedron 2005, 61, 2779.
31. (d) Palacios, F.; Ochoa de Retana, A. M.; Pascual, S.; Oyarzabal, J. J. Org. Chem. 2004, 69, 8767.
32. (e) Palacios, F.; Ochoa de Retana, A. M.; Pascual, S.; Oyarzabal, J. Org. Lett. 2002, 4, 769.
33. Palacios, F.; Vicario, J. Org. Lett. 2006, 8, 5405.
34. The absolute configuration of the stereogenic center of α-dehydroamino esters 2 was established by comparison of the rotary power of the known carboxylic acid resulting from ozonolysis and subsequent oxidation of the intermediate aldehyde.
35. The conventional process involves the addition of a solution of 1-azadiene 1 to a toluene solution of diethylzinc together with the copper catalyst.