Asymmetric synthesis of β-amino acid and amide derivatives by catalytic conjugate addition of aromatic amines to N-alkenoylcarbamates

European Journal of Organic Chemistry

Volumn , Issue 5, 2004, Pages 959-964

  Li, Kelin ^a   Cheng, Xiaohui ^b   Hii, King Kuok ^c  

^a KING'S COLLEGE LONDON   (United Kingdom)

^b NANKAI UNIVERSITY   (China)

^c IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

Amino acids; Asymmetric catalysis; Enantioselectivity; Hydroamination; Palladium

Indexed keywords

AMIDE; AMINE; AROMATIC COMPOUND; BETA AMINO ACID; CARBAMIC ACID DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CONJUGATION; ENANTIOSELECTIVITY; ROOM TEMPERATURE; SPECTRUM;

EID: 2942594935     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300740     Document Type: Article

References (14)

1. Recent reviews: [1a] J. Brunet, D. Neibecker in Catalytic Heterofunctionalization, A. Togni, H. Grützmacher (Eds.), Wiley-VCH, Weinheim, 2001, pp. 91-141.
2. [1b] M. Beller, M. Eishberger, C. G. Hartung, J. Seayad, O. R. Thiel, A. Tillack, H. Trauthwein, Synlett 2002, 1579-1594.
3. [1c] M. Nobis, B. Drießen-Holscher, Angew. Chem. 2001, 113, 4105-4106, Angew. Chem. Int. Ed. 2001, 40, 3983-3985.
4. [1c] M. Nobis, B. Drießen-Holscher, Angew. Chem. 2001, 113, 4105-4106, Angew. Chem. Int. Ed. 2001, 40, 3983-3985.
5. R. Dorta, P. Egli, F. Zurcher, A. Togni, J. Am. Chem. Soc. 1997, 119, 10857-10858.
6. O. Löber, M. Kawatsura, J. F. Hartwig, J. Am. Chem. Soc. 2001, 123, 4366-4367.
7. W. Zhuang, R. G. Hazell, K. A. Jørgensen, Chem. Commun. 2001, 1240-1241.
8. K. Li, K. K. Hii, Chem. Commun. 2003, 1132-1133.
9. D. Ma, J. Jiang, Tetrahedron: Asymmetry 1998, 9, 1137-1142.
10. D. Ma, C. Xia, Org. Lett. 2001, 3, 2583-2586.
11. 20 value for compound 6 is considerably higher than that reported.[6,7] Racemisation of amino acids has been known to occur in copper-catalysed N-arylation reactions: J. B. Clement, J. F. Hayes, H. M. Sheldrake, P. W. Sheldrake, A. S. Wells, Synlett 2001, 1423-1427.
12. Review on the asymmetric synthesis of β-amino acid derivatives: M. Liu, M. P. Sibi, Tetrahedron 2002, 58, 7991-8035.
13. III(salen) complex-catalysed conjugate addition of hydrazoic acid to activated α,β-unsaturated imides had been reported as a method for the synthesis of β-amino acid derivatives: J. K. Myers, E. N. Jacobsen, J. Am. Chem. Soc. 1999, 121, 8959-8960.
14. K. Li, P. N. Horton, M. B. Hursthouse, K. K. Hii, J. Organomet. Chem. 2003, 665, 250-258.