Efficient rhodium-catalyzed asymmetric hydrogenation for the synthesis of a new class of N-aryl β-amino acid derivatives

Organic Letters

Volumn 7, Issue 23, 2005, Pages 5343-5345

  Dai, Qian ^a   Yang, Weiran ^a   Zhang, Xumu ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; RHODIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CLASSIFICATION; HYDROGENATION; STEREOISOMERISM; SYNTHESIS;

AMINO ACIDS; CATALYSIS; HYDROGENATION; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; RHODIUM; STEREOISOMERISM;

EID: 28244456285     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0523897     Document Type: Article

References (24)

1. (a) Hoekstra, W. J., Ed. The Chemistry and Biology of β-Amino Acids. Curr. Med. Chem. 1999, 6, 905.
2. (b) Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997.
3. (c) Ma, J. Angew. Chem., Int. Ed. 2003, 42, 4290.
4. (a) Dumas, F.; Mezrhab, B.; d'Angelo, J.; Riche, C.; Chiaroni, A. J. Org. Chem. 1996, 61, 2293.
5. (b) Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431.
6. (c) Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 12.
7. (d) Zhou, Y.; Tang, W.; Wang, W.; Li, W.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 4952.
8. (e) Tang, W.; Wang, W.; Chi, Y.; Zhang, X. Angew. Chem., Int. Ed. 2003, 42, 3509.
9. (f) Tang, W.; Wu, S.; Zhang, X. J. Am. Chem. Soc. 2003, 125, 9570.
10. (g) You, J.; Drexler, H.; Zhang, S.; Fischer, C.; Heller, D. Angew. Chem., Int. Ed. 2003, 42, 913.
11. (a) Halpern, J. Science 1982, 217, 401.
12. (b) Lubell, W. D.; Kitamura, M.; Noyori, R. Tetrahedron: Asymmetry 1991, 2, 543.
13. Burk, M. J.; Casy, G.; Johnson, N. B. J. Org. Chem. 1998, 63, 6084.
14. For previous examples of asymmetric hydrogenation of electron-rich N-alkyl and N,N-dialkyl enamines, see: (a) Lee, N. E.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 5985.
15. (b) Tararov, V. I.; Kadyrov, R.; Riermeier, T. H.; Holz, J.; Börner, A. Tetrahedron Lett. 2000, 41, 2351.
16. (a) Pozza, M. F.; Zimmermann, K.; Bischoff, S.; Lingenhohl, K. Prog. Neuro-Psychopharmacol. Biol. Psychiatry 2000, 24, 647.
17. (b) Zhi, L.; Tegley, C. M.; Marschke, K. B.; Jones, T. K. Bioorg. Med. Chem. Lett. 1999, 1009.
18. Hsiao, Y.; Rivera, N. R.; Rosner, T.; Krska, S. W.; Njolito, E.; Wang, F.; Sun, Y.; Armstrong, J. D., III.; Grabowski, E. J. J.; Tillyer, R. D.; Spindler, F.; Malan, C. J. Am. Chem. Soc. 2004, 126, 9918.
19. (a) Tang, W.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 1612.
20. (b) Liu, D.; Zhang, X. Eur. J. Org. Chem. 2005, 646.
21. Brandt, C. A.; Silva, A. C.; Pancote, C. G.; Brito, C. L.; Solveira, M. Synthesis 2004, 10, 1557.
22. Xie, W.; Fang, J.; Li, J.; Wang, P. G. Tetrahedron 1999, 55, 12929.
23. (a) Zhang, Z.; Qian, H.; Longmire, J.; Zhang, X. J. Org. Chem. 2000, 65, 6223.
24. (b) Tang, W.; Wu, S.; Zhang, X. J. Am. Chem. Soc. 2003, 125, 9570.