First amidocarbonylation with nitriles for the synthesis of N-acyl amino acids

Synlett

Volumn , Issue 1, 1999, Pages 108-110

  Beller, M ^a   Eckert, M ^a   Moradi, W A ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

Amidocarbonylation; Amino acids; Homogenous catalysis; Nitriles; Palladium

Indexed keywords

ALDEHYDE; AMIDE; AMINO ACID; CARBON MONOXIDE; NITRILE; PALLADIUM;

ACYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROLYSIS; ORGANIC CHEMISTRY; SYNTHESIS;

EID: 0032934226     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2524     Document Type: Article

References (33)

1. Part 9 of the Series "Palladium-Catalyzed Reactions for Fine Chemical Synthesis". For part 8 see Beller, M.; Eckert, M.; Holla, W. E. J. Org. Chem. 1998, 63, 5658.
2. Part 9 of the Series "Palladium-Catalyzed Reactions for Fine Chemical Synthesis". For part 8 see Beller, M.; Eckert, M.; Holla, W. E. J. Org. Chem. 1998, 63, 5658.
3. a) Williams, R. M. Synthesis of Optically Active α-Amino Acids in Organic Chemistry Series, Vol. 7, Eds. Baldwin, J. E.; Magnus, P. D.; Pergamon, 1989.
4. b) Williams, R. M.; Hendrix, J. A. Chem. Rev. 1992, 92, 889.
5. c) Duthaler, R. O. Tetrahedron 1994, 50, 1539.
6. th Ed., Wissenschaftliche Verlagsgesellschaft, Stuttgart, 1986.
7. Jakubke, H.-D. Peptide: Chemie und Biologie, Spektrum, Akad. Verl. Heidelberg, Berlin, Oxford, 1996, p. 313.
8. Mikhalkin, A. P. Russ. Chem. Rev. 1995, 64, 259.
9. Strecker, A. Liebigs Ann. Chem. 1850, 75, 57.
10. Wakamatsu, H.; Uda, J.; Yamakami, N. J. Chem. Soc., Chem. Commun. 1971, 1540.
11. For reviews see: a) Kühlein, K.; Geissler, H. Amidocarbonylation in Transition Metals for Organic Synthesis, Eds. Beller, M.; Bolm, C. Wiley-VCH, Weinheim, 1998, Vol. 1, p.79.
12. b) Knifton, J. F. in Applied Homogeneous Catalysis with Metal Complexes, Eds. Herrmann, W. A.; Cornils, B. Wiley-VCH, Weinheim, 1996, p. 159.
13. c) Ojima, I.; Zhang, Z.; Korda, A.; Ingallina, P.; Clos, N. New carbonylations catalyzed by transition metal complexes in Moser, Eds. W. R.; Slocum, D. W., Homogeneous Transition Met. Catal. React. 1992, 277.
14. d) Lin, J. J.; Knifton, J. F. Amidocarbonylation: Catalyst, Reaction Scope, and Industrial Application in Moser, Eds. W. R.; Slocum, D. W.; Homogeneous Transition Met. Catal. React. 1992, 235.
15. e) Lin, J. J.; Knifton, J. F. CHEMTECH 1992, 22, 248.
16. f) Izawa, K. Yuki Gosei Kagaku Kyokaishi 1988, 46, 218.
17. g) Ojima, I. Chem. Rev. 1988, 88, 1011.
18. h) Ojima, I. J. Mol. Catal. 1986, 37, 25.
19. a) Beller, M.; Eckert, M.; Vollmüller, F.; Bogdanovic, S.; Geissler, H. Angew. Chem., Int. Ed. Engl. 1997, 35, 1494.
20. b) Beller, M.; Eckert, M.; Vollmüller, F. J. Mol. Catal. 1998, 135, 23.
21. c) Beller, M.; Eckert, M.; Holla, E. W. J. Org. Chem. 1998, 63, 5658.
22. d) Beller, M.; Eckert, M.; Geissler, H.; Napiersiki, B.; Rebenstock, H.-P.; Holla, W. E. Chem. Eur. J. 1998, 4, 935.
23. a) Vries, J. G. de; Boer, R. P. de; Hogeweg, M.; Gielens, E. E. C. G. J. Org. Chem. 1996, 61, 1842.
24. b) Jägers, E.; Böhshar, M.; Kleiner, H.-J.; Knoll, H.-P.; DE 3913891, 1990.
25. c) Ojima, I.; Okabe, M.; Kato, K.; Kwon, H. B.; Horvath, I. T. J. Am. Chem. Soc. 1988, 110, 150.
26. d) Ojima, I.; Hirai, K.; Fujita, M.; Fuchikami, T. J. Organomet. Chem. 1985, 279, 203.
27. e) Ojima, I.; Kirai, K.; Sagamihara, K. Tetrahedron Lett. 1982, 23, 2491.
28. a) Hall, J. H.; Gisler M. J. Org. Chem. 1976, 41, 3769.
29. b) Gro ziak, M. P.; Chem, J.-W., Townsend, L. B. J. Org. Chem. 1986, 51, 1065.
30. c) Hauser, C. R.; Hoffenberg, S. J. Org. Chem. 1955, 20, 1448.
31. d) Ravindranathan, M.; Sivaram, S. J. Org. Chem. 1982, 47, 4812.
32. Becke, F.; Gnad, J. Liebigs Ann. Chem. 1968, 713, 212-214.
33. Becke, F.; Fleig, H.; Päßler, P. Liebigs Ann. Chem. 1971, 749 198-201.