Unusual amino acids VI. Substituted arylamino acids by asymmetric hydrogenation of N-Cbz and N-Boc protected dehydroamino acid derivatives

Chirality

Volumn 8, Issue 2, 1996, Pages 173-188

  Krause, H W ^a   Kreuzfeld, H J ^a   Schmidt, U ^a   Dobler Ch ^a   Michalik, M ^a   Taudien, S ^a   Fischer, Ch ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

amino acids; aminophosphine phosphinite; chiral rhodium complexes; D and L enantiomers; NMR spectra

Indexed keywords

ALANINE DERIVATIVE; AMINO ACID; AMINO ACID DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; ENANTIOMER; HYDROGENATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0029880204     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1996)8:2<173::AID-CHIR2>3.0.CO;2-K     Document Type: Article

References (38)

1. Brunner, H., Zettlmeier, W. Handbook of Enantioselective Catalysis. Weinheim: VCH Verlags-gesellschaft, 1993.
2. Taudien, S., Schinkowski, K., Krause, H. W. Asymmetric synthesis of 3-arylalanines. Tetrahedron Asym. 4:73-84, 1993.
3. Krause, H. W., Wilcke, F. W., Kreuzfeld, H.-J., Döbler, Ch. Asymmetric synthesis of furylalanine derivatives. Chirality 4:110-115, 1992.
4. Döbler, Ch., Kreuzfeld, H.-J., Krause, H. W., Michalik, M. Asymmetric synthesis of thienylalanines. Tetrahedron Asym. 4:1833-1842, 1993.
5. Krause, H. W., Kreuzfeld, H.-J., Döbler, Ch., Taudien, S. Asymmetric synthesis of fluorine containing phenylalanines. Tetrahedron Asym. 3:555-566, 1992.
6. Kagan, H. B. In: Asymmetric Synthesis. Morrison, J. D., ed. New York: Academic Press, 1985: Vol. 5, Chap. 1.
7. (a) Halpern, J. In: Asymmetric Synthesis. Morrison, J. D., ed. New York: Academic Press, 1985: Vol. 5, Chap. 5.
8. (b) Landis, C. R., Halpern, J. Asymmetric hydrogenation of methyl-(Z)-α-acetamidocinnamate catalyzed by {1,2-bis((phenyl-o-anisoyl)phosphino)ethane}-rhodium(I): Kinetics, mechanism and origin of enantioselection. J. Am. Chem. Soc. 109: 1746-1754, 1987.
9. (c) Ojima, I., Kogure, T., Yoda, N. Asymmetric hydrogenation of prochiral olefins catalyzed by rhodium complexes with chiral pyrrolidinodiphosphines. Crucial factors for the effective asymmetric induction. J Org. Chem. 45:4728-4739, 1980.
10. (d) Brown, J. M., Chaloner, P. A. Structural characterisation of a transient intermediate in rhodium-catalysed asymmetric homogeneous hydrogenation. J. Chem. Soc., Chem. Commun. 344-346, 1980.
11. (e) Brown, J. M., Murrer, B. A. The mechanism of asymmetric hydrogenation. Chiral bis(diphenylphosphino)-α-phenylalkane complexes in catalytic and structural studies. J. Chem. Soc. Perkin Trans. II 489-497, 1982.
12. (f) Chan, A. S. C., Pluth, J. J., Halpern, J. Identification of the enantioselective step in the asymmetric catalytic hydrogenation of a prochiral olefin. J. Am. Chem. Soc. 102:5952-5954, 1980.
13. (g) Nagel, U., Rieger, B. The catalytic hydrogenation of α-acetyl-ammocinnamic acid with rhodium-(I)-bis(phosphine) complexes, the origin of the enantioselection. Organometallics 8:1534-1538, 1989.
14. Kreuzfeld, H.-J., Döbler, Ch., Krause, H. W., Facklam, Ch. Asymmetric hydrogenation of (Z)-N-acylaminocinnamic acid derivatives bearing different protective groups. Tetrahedron Asym. 4:2047-2051, 1993.
15. (a) Schmidt, U., Weller, D., Holder, A., Lieberknecht, A. Total synthesis of 4949-III, a natural inhibitor of aminopeptidase B from Ehrlich ascites carcinoma cells. Tetrahedron Lett. 29:3223-3230, 1988.
16. (b) Melillo, D., Larsen, R. D., Mathre, D. J., Shukis, W. F., Wood, A. W., Colleluori, J. R. Practical enantioselective synthesis of a homotyrosine derivative and (R,R)-4-propyl-9-hydroxynaphthoxazine, a potent dopamine agonist. J. Org. Chem. 52:5143-5150, 1987.
17. (c) Schmidt, U., Lieberknecht, A., Kazmaier, U., Gnesser, H., Jung, G., Metzger, J. Amino acids and peptides; 75. Synthesis of di- and trihydroxyamino acids. Construction of lipophilic tripalmitoyldihydroxy-α-amino acids. Synthesis 49-55, 1991.
18. (d) Schmidt, U., Meyer, R., Leitenberger, V., Stabler, F., Lieberknecht, A. Total synthesis of biphenomycins, II. Synthesis of protected (2S,4R)-4-hydroxyornithines. Synthesis 409-413, 1991.
19. (e) Achiwa, K. New chiral phosphine-rhodium catalysts for asymmetric synthesis of (R)- and (S)-N-benzyloxycarbonylalanine. Chem. Lett. 777-778, 1977.
20. (f) Carlström, A. S., Torbjörn, F. Palladium-catalyzed synthesis of dehydroamino acid derivatives. Synthesis 414-418, 1989.
21. 2-symmetric bis(phospholanes): Production of amino acid derivatives via highly enantioselective hydrogenation reactions. J. Am. Chem. Soc. 115:10125-10138, 1983.
22. Giannis, A., Kolter, T. Peptidmimetica für Receptorliganden-Entdeckung, Entwicklung und medizinische Perspektiven. Angew. Chem. 103: 1303-1325, 1993.
23. See, for example, (a) Coppola, G. M., Schuster, H. F. Asymmetric Synthesis. Construction of Chiral Molecules Using Amino Acids. New York: John Wiley, 1987.
24. (b) Spatola, A. F. In: Chemistry and Biochemistry of Amino Acids, Peptides and Proteins. Weinstein, B., ed. New York: Marcel Dekker, 1983: Vol. 7, 267-357.
25. Kagan, H. B., Dang, T. P. Asymmetric catalytic reduction with transition metal complexes I. A catalytic system of rhodium (I) with (.)-2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane, a new chiral diphosphine. J. Am. Chem. Soc. 94:6429-6433, 1972.
26. Krause, H. W., Foken, H., Pracejus, H. Aminophosphine phosphinites of propranolol as ligands for rhodium catalyzed asymmetric hydrogenation of dehydroamino acids. New J. Chem. 13:615-620, 1989.
27. (a) Schmidt, U., Lieberknecht, A., Schanbacher, U., Beuttler, T., Wied, J. Einfache Herstellung von N-Acyl-2-(diethoxyphosphoryl)-glycinestern und ihre Verwendung zum Aufbau von Dehydroaminosäureestern. Angew. Chem. 94:797-798, 1982.
28. (b) Schmidt, U , Lieberknecht, A., Wild, J. Amino acids and peptides XLIII. Dehydroamino acids XVIII. Synthesis of dehydroamino acids and amino acids from N-acyl-2(dialkyloxy-phosphinyl)giycin esters, II. Synthesis 53-60, 1984.
29. (c) Schmidt, U., Griesser, H., Leitenberger, V., Lieberknecht, A., Mangold, R., Meyer, R., Riedl, B. Diastereoselective formation of (Z)-didehydroamino acid esters. Synthesis 487-490, 1992.
30. Ciattini, P. G., Morera, E., Ortar, G. Horner synthesis of dihydroamino acid derivatives in a liquid-liquid two-phase system. Synthesis 140-142, 1988.
31. Shin, Chung-gi., Yonezawa, Y., Watanabe, E. Convenient synthesis and reaction of various kinds of α-dehydroglutamic acid derivatives. Tetrahedron Lett. 26:85-88, 1985.
32. Henzl, M. R., Corson, S. L., Moghissi, K., Buttram, V. C., Berquist, C., Jacobson, J. Administration of nasal nafarelin as compared with oral danazol for endometriosis. A multicenter double-blind comparative clinical trial. N. Engl. J. Med. 318:485, 1988.
33. Hsieh, K.-Ch., LaHann, T., Speth, R. J. J. Topographic probes of angiotensin and receptor: potent angiotensin II agonist containing diphenylalanine and long-acting antagonists containing biphenylalanine and 2-indan amino acid in position 8. Med Chem. 32:898, 1989.
34. Eilliams, D., Kannan, R. Stereochemistry of the cyclic tripeptide antibiotic WS-43708A. J. Org. Chem. 52:5435-5437, 1987.
35. Yabe, Y., Miura, C., Horikoshi, H., Baba, Y. Analogs of luteinizing hormonereleasing hormone with modification in position 3. Chem. Pharm. Bull. 24:3149-3157, 1976.
36. Hsieh, W.-Ch., Carlson, J. A. A simple asymmetric synthesis of 4-arylphenylalanines via palladium catalyzed cross-coupling reaction of arylboronic acids with tyrosine triflate. J. Org. Chem. 57:379-381, 1992.
37. Pretsch, E., Clerc, T., Seibl, J., Simon, W. Tabellen zur Strukturaufklärung organischer Verbindungen mit spektroskopischen Methoden, 3. Auflage, Springer-Verlag H 245, H 255, H 357, 1986.
38. Günther, H. NMR-Spektroskopie. Stuttgart: Georg-Thieme Verlag, 1992.