Palladium-Catalyzed Amidocarbonylation - A New, Efficient Synthesis of N-Acyl Amino Acids

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 13-14, 1997, Pages 1494-1496

  Beller, Matthias ^a   Eckert, Markus ^a   Vollmüller, Frank ^a   Bogdanovic, Sandra ^b   Geissler, Holger ^b  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^b SANOFI   (France)

Author keywords

Amino acids; Carbonylations; Homogeneous catalysis; Multicomponent reactions; Palladium

Indexed keywords

EID: 0030851133     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199714941     Document Type: Article

References (30)

1. a) M. Baviere, B. Durif-Varambon (Institute Français du Pétrole), DE-3514329, 1985 [Chem. Abstr. 1985, 103, 8767w];
2. b) C. Theis, W. Latz (Hüls AG), DE-3643204, 1986 [Chem Abstr. 1988, 109, 170928v];
3. c) J. J. Lin (Texaco Inc.), US-4720573, 1988 [Chem Abstr. 1988, 109, 38240k].
4. a) H. Kessler, Angew. Chem. 1993, 105, 572; Angew. Chem. Int. Ed. Engl. 1993, 32, 543;
5. a) H. Kessler, Angew. Chem. 1993, 105, 572; Angew. Chem. Int. Ed. Engl. 1993, 32, 543;
6. b) J. Gante, ibid. 1994, 106, 1780-1802 and 1994, 33, 1699-1721;
7. b) J. Gante, ibid. 1994, 106, 1780-1802 and 1994, 33, 1699-1721;
8. c) A. Giannis, T. Kolter, ibid. 1993, 103, 1303-1326 and 1993, 32, 1244.
9. c) A. Giannis, T. Kolter, ibid. 1993, 103, 1303-1326 and 1993, 32, 1244.
10. a) U. Kazmaier, J. Org. Chem. 1996, 61, 3694;
11. b) U. Kazmaier, A. Krebs, Angew. Chem. 1995, 107, 2213; Angew. Chem. Int. Ed. Engl. 1995, 34, 2012;
12. b) U. Kazmaier, A. Krebs, Angew. Chem. 1995, 107, 2213; Angew. Chem. Int. Ed. Engl. 1995, 34, 2012;
13. c) R. M. Williams, Synthesis of Optically Active α-Amino Acids, Vol. 7 in Organic Chemistry Series (Eds.: J. E. Baldwin, P.D. Magnus), Pergamon, Oxford, 1989;
14. d) R. M. Williams, M.-N. Im, J. Am. Chem. Soc. 1991, 113, 9276.
15. a) M. Beller, B. Cornils, C. D. Frohning, C. W. Kohlpaintner, J. Mol. Catal. 1995, 104, 17-85;
16. b) I. Ugi, Proc. Estonian Acad. Sci. Chem. 1995, 44, 237-273;
17. c) B. Cornils, W. A. Herrmann, Quo vadis?in Applied Homogeneous Catalysis with Metal Complexes (Eds.: B. Cornils, W. A. Herrmann), VCH, Weinheim, 1996.
18. a) H. Wakamatsu, J. Uda, N. Yamakami, J. Chem. Soc. Chem. Commun. 1971, 1540;
19. b) I. Ojima, Chem. Rev. 1988, 88, 1011;
20. c) J. F. Knifton, Amidocarbonylation in Applied Homogeneous Catalysis with Metal Complexes (Eds.: B. Cornils, W. A. Herrmann), VCH, Weinheim, 1996.
21. J. Ojima, Z. Zhang, Organometallics 1990, 9, 3122-3127.
22. We would like to thank E. Jägers (Hoechst AG) for carrying out the first amidocarbonylation trials with non-cobalt catalysts; E. Jägers, H.-P. Koll (Hoechst AG), EP-338330 1989 [Chem. Abstr. 1990, 112, 77951z].
23. K. Izawa, J. Synth. Org. Chem. 1988, 46, 218-231.
24. a) D. L. Boger, R. M. Borzilleri, S. Nukui, J. Org. Chem. 1996, 61, 3561;
25. b) K. Burgess, D. Lim, C. I. Martinez, Angew. Chem. 1996, 108, 1162; Angew. Chem. Int. Ed. Engl. 1996, 35, 1077 .
26. b) K. Burgess, D. Lim, C. I. Martinez, Angew. Chem. 1996, 108, 1162; Angew. Chem. Int. Ed. Engl. 1996, 35, 1077 .
27. a) M. Beller, H. Fischer, P. Gross, T. Gerdau, H. Geissler, S. Bogdanovic (Hoechst AG), DE-4415712, 1995 [Chem. Abstr. 1996, 124, 149264a];
28. b) E. Drent, E. Kragtwijk (Shell), GB-2252770, 1991 [Chem. Abstr. 1993, 118, 39410p].
29. a) J.-J. Parnaud, G. Campari, P. Pino, J. Mol. Catal. 1979, 6, 341;
30. b) P. Magnus, M. Slater, Tetrahedron Lett. 1987, 28, 2829.