The first highly enantioselective homogeneously catalyzed asymmetric reductive amination: Synthesis of α-N-benzylamino acids

Journal of Organic Chemistry

Volumn 68, Issue 10, 2003, Pages 4067-4070

  Kadyrov, Renat ^a   Riermeier, Thomas H ^a   Dingerdissen, Uwe ^a   Tararov, Vitali ^b   Börner, Armin ^b  

^a EVONIK INDUSTRIES AG   (Germany)

^b UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; CATALYSIS; SYNTHESIS (CHEMICAL);

HOMOGENEOUS CATALYSTS;

ORGANIC ACIDS;

2 OXOACID; ALPHA AMINO ACID; ALPHA N BENZYLAMINO ACID DERIVATIVE; AMINO ACID DERIVATIVE; BENZYLAMINE; CATION; LIGAND; RHODIUM COMPLEX; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; REACTION ANALYSIS; REDUCTION; SYNTHESIS; TECHNIQUE;

EID: 0037950624     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020690k     Document Type: Article

References (25)

1. (a) Tarasevich, V. A.; Kozlov, N. G. Russ. Chem. Rev. 1999, 68, 55-72.
2. (b) Rylander, P. N. Hydrogenation Methods; Academic Press: New York, 1985; pp 82-93.
3. (c) Emerson, W. S. Org. React. 1948, 4, 174-255.
4. (a) Marko, L.; Bakos, J. J. Organomet. Chem. 1974, 81, 411-414.
5. (b) Klyuev, M. V.; Khidekel, M. L. Transition Met. Chem. 1980, 5, 134-139.
6. (c) Blaser, H.-U.; Buser, H.-P.; Jalett, H.-P.; Pugin, B.; Spindler, F. Synlett 1999, 867-868.
7. (d) Margalef-Catala, R.; Claver, C.; Salagre, P.; Fernandez, E. Tetrahedron Lett. 2000, 41, 6583-6588.
8. (a) Lin, Y.-S.; Yamamoto A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; John Wiley & Sons: Hoboken, 2002; pp 2399-2423.
9. (b) Nikalje, M. D.; Ali, I. S.; Dewkar, G. K.; Sudalai, A. Tetrahedron Lett. 2000, 41, 959-961.
10. (c) Lower, E. S. Riv. Ital. Sostanze Grasse 1996, 73, 469-474.
11. (d) Collin, J. Bull. Soc. Chim. Fr. 1988, 976-781.
12. (e) Chipens, G.; Slavinska, V.; Kreile, D.; Sile, D.; Krumina, L.; Strautina, A.; Karahanov, R. Latv. PSR Zinat. Akad. Vestis, Kim. Ser. 1988, 515-535.
13. (f) Cooper, A. J. L.; Ginos, J. Z.; Meister, A. Chem. Rev. 1983, 83, 321-358.
14. Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon Press: Oxford, 1988; pp 1-380.
15. (a) Tararov, V. I.; Kadyrov, R.; Riermeier, T. H.; Börner, A. Chem. Commun. 2000, 1867-1868.
16. (b) Tararov, V. I.; Kadyrov, R.; Riermeier, T. H.; Börner, A. Adv. Synth. Catal. 2002, 344, 200-208.
17. Brunner, H.; Pieronczyk, W.; Schönhammer, B.; Streng, K.; Bernal, I.; Korp, J. Chem. Ber. 1981, 114, 1137-1149.
18. Bergens, S. H.; Whelan, J.; Bosnich, B. Inorg. Synth. 1997, 31, 131-138.
19. Nagel, U.; Kinzel, E.; Andrade, J.; Prescher, G. Chem. Ber. 1986, 119, 3326-3343.
20. Fryzuk, M. D.; Bosnich, B. J. Am. Chem. Soc. 1978, 100, 5491-5494.
21. Bosch, B. E.; Trauthwein, H.; Riermeier, T.; Dingerdissen, U.; Monsees, A. (Aventis Research & Technologies Gmbh & Co Kg, Germany). Ger. Patent. DE 19918420, 2000.
22. Spindler, F.; Wirth-Tijani, A.; Landert, H. (Ciba-Geigy A.-G., Switz.) EP 612758 1994.
23. (a) Quitt, P.; Hellerbach, J.; Vogler, K. Helv. Chim. Acta 1963, 46, 327-333;
24. (b) Hassan, N. A.; Bayer, E.; Jochims, J. C. J. Chem. Soc., Perkin Trans. 1 1998, 3747-3758.
25. (c) Petersen, J. S.; Fels, G.; Rapoport, H. J. Am. Chem. Soc. 1984, 106, 4539-4547.