Enantioselective synthesis of α-aminophosphonic acid derivatives by hydrogenation

Chirality

Volumn 10, Issue 7, 1998, Pages 564-572

  Schmidt, Ute ^a   Krause, Hans Walter ^a   Oehme, Günther ^a,b   Michalik, Manfred ^a   Fischer, Christine ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b NONE   (Germany)

Author keywords

Aminophosphine phosphinites; Asymmetric hydrogenation; Dehydro aminophosphonic acids; NMR; Rhodium complexes

Indexed keywords

PHOSPHORAMIDIC ACID DERIVATIVE; PROPRANOLOL;

CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHIRALITY; CONFERENCE PAPER; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; HYDROGENATION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0031683162     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1998)10:7<564::AID-CHIR3>3.0.CO;2-2     Document Type: Conference Paper

References (45)

1. a) Kafarski, P., Lejczak, B. Biological activity of aminophosphonic acids. Phosphorus Sulfur Silicon 63:193-215, 1991.
2. b) Kafarski, P., Mastalerz, P. Aminophosphonates: natural occurrence biochemistry and biological properties. In: Beiträge zur Wirkstofforschung, Vol. 21. Oehme, P., Löwe, H., Göres, E., eds. J. Axt. Inst. Wirkstofforschung, Berlin, 1984.
3. a) Atherton, F.R., Hassall, C.H., Lambert, R.W. Synthesis and structure-activity relationship of antibacterial phosphonopeptides incorporating (l-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid. J. Med. Chem. 29:29-40, 1986.
4. b) Allen, J.G., Atherton, F.R., Hall, M.J., Hassall, C.H., Holmes S.W., Lambert, R.W., Nisbet, L.J., Ringrose, P.S. Phosphonopeptides, a new class of synthetic antibacterial agents. Nature 272:56-58, 1978.
5. c) Atherton, F.R., Hall, M.J., Hassall, C.H., Lambert, R.W., Ringrose, P.S. Phosphonopeptides as antibacterial agents: rationale, chemistry, and structure-activity relationship. Antimicrob. Agents Chemother. 15:677-683, 1979.
6. d) Allen, J.G., Atherton, F.R., Hall, M.J., Hassall, C.H., Holmes S.W., Lambert, R.W., Nisbet, L.J., Ringrose, P.S. Phosphonopeptides as antibacterial agents: alaphosphaline and related phosphonopeptides. Antimicrob. Agents Chemother. 15:684-695, 1979.
7. e) Atherton, F.R., Hall, M.J., Hassall, C.H., Lambert, R.W., Lloyd, W.J., Ringrose, P.S. Phosphonopeptides as antibacterial agents: mechanism of action of alaphosphalin. Antimicrob. Agents Chemother. 15:696-705, 1979.
8. Kase, K., Yamato, M., Koguchi, T., Okachi, R., Kasai, M., Shirahata, K., Kawamoto, I., Shuto, K., Karasawa, A. et al. Phosphorus-containing oligopeptides and a pharmaceutical composition containing them. Eur. Pat. Appl. EP 61172, 1982.
9. a) Bird, J., De Nello, R., Harper, G.P., Hunter, D.J., Karran, E.H., Markwell, R.E., Miles-Williams A.J., Rahman, S.S., Ward, R.W. Synthesis of novel N-phosphono-alkyl dipeptide inhibitors of human collagen-ese. J. Med. Chem. 37:158-169, 1994.
10. b) McLeod, D.A. Brinkworth, R.L., Ashley J.A., Janda, K.D., Wirsching, P. Phosphonamidates and phosphonamidatesters as HIV-1 proteaseinhibitors. Bioorg. Med. Chem. Lett. 1:653-658, 1991.
11. For comprehensive reviews see: a) Dhawan, B., Redmore, D. Optically active l-aminoalkylphosphonic acids. Phosphorus Sulfur Silicon 32: 119-144, 1987. b) Kukhar, V.P., Soloshonok, V.A., Solodenko, V.A. Asymmetric synthesis of phosphorus analogs of amino acids. Phosphorus Sulfur Silicon 92:239-264, 1994.
12. For comprehensive reviews see: a) Dhawan, B., Redmore, D. Optically active l-aminoalkylphosphonic acids. Phosphorus Sulfur Silicon 32: 119-144, 1987. b) Kukhar, V.P., Soloshonok, V.A., Solodenko, V.A. Asymmetric synthesis of phosphorus analogs of amino acids. Phosphorus Sulfur Silicon 92:239-264, 1994.
13. a) Belov, Yu. P., Davankov, V.A., Rogozhin, S.V. Optically active α-aminophosphonic acid and their ethylester. Izv. Akad. Nauk. SSSR, Ser. Khim. 7:1596, 1977.
14. b) Rogozhin, S.V., Davankov, V.A., Belov, Yu. P. Optically active diethyl-α-aminobenzylphosphonate Izv. Akad. Nauk, SSSR, Ser. Khim. 4:955-956. 1973.
15. c) Maier, L., Spörri, H. Organic Phosphorus Compounds 96. Resolution of l-amino-2-(4-fluorphenyl)-ethylphosphonic acid as well as some di-and tripeptides. Phosphorus Sulfur Silicon 61:69-75, 1991.
16. Antczak, K., Szewczyk, K. Separation of racemic phosphonic analogues of glutamic acid. Phosphorus Sulfur Silicon 22:247-251, 1985.
17. Gilmore, W.F., McBride, H.A. Synthesis of an optically active α-aminophosphonic acid. J. Am. Chem. Soc. 94:4361, 1972.
18. a) Huber, R., Knierzinger, A., Olbrecht, J.-P., Vasella, A. Nucleophilic additions to N-glycosyl nitrones: Asymmetric synthesis of α-aminophosphonic acids. Helv. Chim. Acta. 68:1730-1747, 1985.
19. b) Huber, R., Vasella, A. Nucleophilic additions to N-glycosyl-nitrones. Asymmetric synthesis of N-hydroxy-α-aminophosphonic and α-aminophosphonic acids. Helv. Chim. Acta. 79:1461-1476, 1987.
20. Smith, A.B., Yager, K.M., Taylor, C.M. Enantioselective synthesis of diverse a-aminophosphonate diesters. J. Am. Chem. Soc 117:10879-10888, 1995.
21. a) Yuan, C., Cui, S. Studies on organophosphorus compounds XLVIII. Structural effect on the induced asymmetric addition of dialkylphosphite to chiral aldirnine derivatives. Phosphorus Sulfur Silicon 55:159-164, 1991.
22. b) Yuan, C., Li, S., Wang, G., Ma, Y. Studies on organophosphorus compounds 78. New aspects on the induced asymmetric addition of dialkyl phosphite to aldimines, an effective synthesis of chiral 1-arylphosphonoglycine derivatives. Phosphorus Sulfur Silicon 81:27-35, 1993.
23. Laschat, S., Kunz, H. Carbohydrates as chiral templates: Stereoselective synthesis of (R)-and (S)-α-aminophosphonic acid derivatives. Synthesis 90-95, 1992.
24. a) Hanessian, S., Bennani, Y.L. Electrophilic amination and azidation of chiral α-alkyl phosphonamides: Asymmetric synthesis of α-amino α-alkyl phosphonic acids. Synthesis 1272-1274, 1994.
25. b) Denmark, S.E., Chatani, N., Pansare, S.V. Asymmetric electrophilic amination of chiral phosphorus-stabilized anions. Tetrahedron 48:2191-2208, 1992.
26. Hanessian, S., Bennani, Y.L. A versatile asymmetric synthesis of α-amino-α-alkyl-phosphonic acids of high enantiomeric purity. Tetrahedron Lett. 31:6455-6468, 1990.
27. Yokumatsu, T., Shibuya, S. Enantioselective synthesis of α-amino phosphonic acids by an application of stereoselective opening of homochiral dioxane acetals with triethylphosphite. Tetrahedron: Asymmetry 3:377-378, 1992.
28. Maury, C., Royer, J., Husson, H.-P. A simple and general method for the asymmetric synthesis of α-aminophosphonic acids. Tetrahedron Lett. 33:6127-6130, 1992.
29. Sting, M., Steglich, W. Phosphoranaloge von Aminosäuren III. Synthese optisch aktiver 1-Aminoalkylphosphonsäuren der (S)-und (R)-Reihe mit Hilfe von (-)-Ephedrin als Auxiliar. Synthesis 132-134, 1990.
30. a) Ferrari, M., Jommi, G., Miglierini, G., Pagliarin, R., Sisti, M. Asymmetric synthesis of diethyl-α-amino-α-alkyl-phosphonates by alkylation of the chiral Schiff base derived from (+)-ketopinic acid and diethyl-aminomethyl phosphonate. Synth. Commun. 22:107-123, 1992.
31. b) Jommi, G., Miglierini, G., Pagliarin, R., Sello, G., Sisti, M. Asymmetric synthesis of diethyl α-amino-α-alkylphosphonates by alkylation of chiral phosphonoglycine equivalents: Role of chelating effects. Tetrahedron: Asymmetry 3:1131-1134, 1992.
32. a) Quazzani, F., Roumestant, M.-L., Viallefont, P., El Hallaqui, A. Synthesis of enantiomerically pure phosphonic analogues of homoserine derivatives. Tetrahedron: Asymmetry 2:913-917, 1991.
33. b) Jacquier, R., Quazzani, F., Roumestant, M.-L., Villefont, P. Synthesis of enantiomerically pure aminophosphonic acids. Phosphorus Sulfur Silicon 36:73-77, 1988.
34. Sasai, H., Arai, S., Tahara, Y., Shibasaki, M. Catalytic asymmetric synthesis of α-aminophosphonates using lanthanoid-potassium-binol complexes. J. Org. Chem. 60:6656-6657, 1995.
35. For a review see: Kreuzfeld, H.-J., Döbler, Ch., Schmidt, U., Krause, H.W. Synthesis of non-proteinogenic D-or L-amino acids by asymmetric hydrogenation. Amino Acids 11:269-282, 1996.
36. Schmidt, U., Oehme, G., Krause, H.W. Catalytic stereoselective synthesis of α-amino phosphonic acid derivatives by asymmetric hydrogenation. Synth. Commun. 26:777-781, 1996.
37. Talley, J.J. Process for making chiral α-amino phosphinates, selected novel chiral α-aminophosphonates. U.S. Pat. 5321153, 1994.
38. Schöllkopf, U., Hoppe, I., Thiele, A. Enantioselective synthesis of L-(1-aminoethyl) phosphonic acid by asymmetric catalytic hydrogenation of N-[1-(dimethoxyphosphoryl)ethyl]-formamide. Liebigs Ann. Chem. 555-559, 1985.
39. Brunner, H., Pieronczyk, W., Schönhammer, B., Streng, K., Bernal, I., Korp, J. Enantioselektive Aminosäuresynthese durch Hydrierung prochiraler Olefine mit Rh-Komplexen des neuen optisch aktiven chelatbildenden Phosphans NORPHOS. Chem. Ber. 114:1137-1149, 1981.
40. Knowles, W.S., Sabacky, M.J., Vineyard, B.D., Weinkauff, D.J. Asymmetric hydrogenation with a complex of rhodium and a chiral bisphosphine. J. Am. Chem. Soc. 97:2567-2568, 1975.
41. a) Brovarets, V.S., Zyuz, K.V., Budnik, L.V., Solodenko, V.A., Drach, B.S. New approach to the synthesis of [1-(acylamino)alkenyl]-phosphonic acids, their analogs, and their derivatives. Zh. Obsh. Khim. 63:1259-1265, 1993.
42. b) Taudien, S., Schinkowski, K., Krause, H.W. Unusual Amino Acids III. Asymmetric synthesis of 3-Arylalanines. Tetrahedron: Asymmetry 4:73-84, 1993.
43. Krause, H.W., Schmidt, U., Taudien, S., Costisella, B., Michalik, M. Aminophosphine phosphinites of propranolol analogues as ligands for rhodium catalyzed asymmetric hydrogenation. J. Mol. Catal. A. 104: 147-157, 1995.
44. Landis, C.R., Halpern, J. Asymmetric hydrogenation of methyl-(Z)-α-acetamido-cinnamate 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.
45. Jackman, L.M., Sternhell, S. Application of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry. Oxford: Pergamon Press, 1969, 352.