Asymmetric synthesis of amino acids by Cr(II) complexes of natural amino acids

Journal of Organometallic Chemistry

Volumn 682, Issue 1-2, 2003, Pages 143-148

  Micskei, Károly ^a   Holczknecht, Orsolya ^a   Hajdu, Csongor ^a   Patonay, Tamás ^a   Marchis, Valér ^a   Meo, Milena ^a,b   Zucchi, Claudia ^b   Pályi, Gyula ^b  

^a UNIVERSITY OF DEBRECEN   (Hungary)

^b UNIVERSITY OF MODENA AND REGGIO EMILIA   (Italy)

Author keywords

Amino acid complexes; Chromium(II); Oxime reduction; Synthesis; Amino acids

Indexed keywords

ALANINE; AMINO ACID DERIVATIVE; ASPARTIC ACID; CARBON; CHROMIUM DERIVATIVE; HISTIDINE; NITROGEN; ORGANOMETALLIC COMPOUND; OXIME DERIVATIVE; PHENYLACETIC ACID DERIVATIVE; PHENYLALANINE; PHENYLPROPIONIC ACID DERIVATIVE; PROPIONIC ACID DERIVATIVE; REDUCING AGENT; VALINE;

AMINO ACID SYNTHESIS; AQUEOUS SOLUTION; CHEMICAL BINDING; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; ENANTIOMER; OXIDATION REDUCTION REACTION; REVIEW; STOICHIOMETRY; STRUCTURE ANALYSIS;

EID: 0141515561     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(03)00775-7     Document Type: Article

References (62)

1. Hanessian S. Total Synthesis of Natural Products: The Chiron Approach 1983 Pergamon Oxford
2. Gawley R.E. Aubé J. Principles of Asymmetric Synthesis 1996 Pergamon-Elsevier Oxford
3. Stephenson G.R. (Ed.), Advanced Asymmetric Synthesis, Blackie Academic & Professional, London, 1996.
4. Stinson, S.C. Chem. Eng. News, Sept. 21 (1998) 83; Oct. 11 (1999) 101; May 8 (2000) 59; July 10 (2000) 63; Oct. 23 ( 2000) 55; Oct. 1 (2001) 79
5. Jacoby, M. Chem. Eng. News, March 25 (2002) 43
6. Rouhi, A.M. Chem. Eng. News, June 10 (2002) 43; June 10 (2002) 51.
7. Brunner H. Zettlmeier W. Handbook of Enantioselective Catalysis I-II 1993 VCH Weinheim
8. Sheldon R.A. Chirotechnology 1993 M. Dekker New York
9. Ojima J. (Ed.), Catalytic Asymmetric Synthesis, Pergamon-Elsevier, Oxford, 1993.
10. Burger K. (Ed.), Biocoordination Chemistry: Coordination Equilibria in Biologically Active Systems, E. Horwood, New York, 1990
11. Iakovidis A. Hadjiliadi N. Coord. Chem. Rev. 135/136 1994 17
12. Nakagawa M. Nakao H. Watanabe K. Chem. Lett. 1985 391
13. Wilkinson, G. Gillard, R.D. Mc Cleverty J.A. (Eds.), Comprehensive Coordination Chemistry, Pergamon, Oxford, 1987, Vol. 2, pp. 739
14. Harada K. Munegumi T. in: Trost B.M. Fleming I. (Eds.) Comprehensive Organic Synthesis 8 1991 139-158 Pergamon London
15. Carmona D. Lahoz F.J. Atencio R. Oro L.A. Lamata L.P. José E.S. Tetrahedron: Asymmetry 4 1993 1425
16. Kikuchi J.-i. Zhang Z.Y. Murakami Y. J. Am. Chem. Soc. 117 1995 5383
17. Wächterchäuser G. Proc. Natl. Acad. Sci. USA 87 1990 200
18. Wächterchäuser G. Progr. Biophys. Mol. Biol. 58 1992 85
19. Wächterchäuser G. Science 289 2000 1307
20. Huber C. Wächterchäuser G. Science 276 1997 245
21. Huber C. Wächterchäuser G. Science 281 1998 670
22. Crabtree R.H. Science 276 1997 222
23. Cody G.D. Boctor N.Z. Filley T.R. Hazen R.M. Scott J.H. Sharma A. Yoder H.S. Jr. Science 289 2000 1337
24. Gyarmati J. Hajdú C. Dinya Z. Micskei K. Zucchi C. Pályi G. J. Organomet. Chem. 586 1999 106
25. PatonayT. Hajdú C. Jekö J. Lévai A. Micskei K. Zucchi C. Tetrahedron Lett. 40 1999 1373
26. Pályi G. Bencze L. Micskei K. Zucchi C. Atti Accad. Nazl. Sci. Lett. Arti (Modena) 317 8/3 2001 457
27. Marchis, V. Diploma (MSc) Thesis, University of Debrecen, Debrecen, 2001
28. Ahmad A. Spenser I.D. Can. J. Chem. 39 1961 1349
29. Micskei K. Debreczeni F. Nagypál I. J. Chem. Soc. Dalton Trans. 1983 1335
30. Zékány L. Nagypál J. in: Leggett D.G. (Ed.) Computational Methods for the Determination of Formation Constants 1985 291-353 Plenum New York
31. Micskei, K. Nagypál, I. J. Chem. Soc. Dalton Trans. (1986) 2721
32. see also T. Kiss, in Ref. [4a] , pp. 56.
33. Marfey P. Carlsberg Res. Commun. 49 1984 591
34. Szókán G. Hadfi S. Krizsán K. Liembeck A. Almás M. Somlai C. J. Liquid Chromatogr. 17 1994 2759
35. Shriver D.F. Drezdzon M.A. Manipulation of Air Sensitive Compounds 2nd ed 1986 Wiley New York
36. Espenson J.H. Acc. Chem. Res. 25 1992 222
37. Kovács G. Gyarmati J. Somsák L. Micskei K. Tetrahedron Lett. 37 1996 1293
38. Kovács G. Micskei K. Tetrahedron Lett. 38 1997 9055
39. Micskei K. Gyarmati J. Kovács G. Makleit S. Simon C. Szabó Z. Marton J. Hosztafi S. Reineke H. Drexler H.J. Eur. J. Org. Chem. 1999 149
40. Fürstner A. Chem. Rev. 99 1999 991
41. Lazcano A. Miller S.L. Cell 85 1996 793
42. Honig B. Sharp K. Yang A.S. J. Phys. Chem. 97 1993 1101
43. Lubineau A. Augé J. Queneau Y. Synthesis 1994 741
44. Barta K. Csékei M. Csihony S. Mehdi H. Horváth I.T. Pusztai Z. Vlád G. Magy. Kém. Lapja 55 2000 173
45. Poliakoff M. Fitzpatrick J.M. Farren T.R. Anastas P.T. Science 297 2002 807
46. Pályi G. Alberts K. Bartik T. Boese R. Fráter G. Herbrich T. Herfurth A. Kriebel C. Sorkau A. Tschoerner C.M. Zucchi C. Organometallics 15 1996 3253
47. Szabó M. Szilágyi R. Bencze L. Boese R. Zucchi C. Caglioti L. Pályi G. Enantiomer 5 2000 549
48. Zucchi C. Boese R. Alberts K. Herbrich T. Tóth G. Bencze L. Pályi G. Eur. J. Inorg. Chem. 2001 2297
49. Timms G.H. Wildsmith E. Tetrahedron Lett. 1971 195
50. Takai K. Katsura N. Kunisada Y. Chem. Commun. 2001 1724
51. Galamb V. Pályi G. Kajtár M. Inorg. Chim. Acta 55 1981 L113
52. Zucchi C. Tiddia S. Boese R. Tschoerner C.M. Bencze L. Pályi G. Chirality 13 2001 458
53. Soai K. Morioka H. Choji K. Nature 378 1995 767
54. Soai K. Shibata T. in: Pályi G. Zucchi C. Caglioti L. (Eds.) Advances in BioChirality 1999 125-136 Elsevier Amsterdam
55. Soai K. Shibata T. Sato I. Acc. Chem. Res. 33 2000 382
56. Soai K. Sato I. Shibata T. Komiya S. Hayashi M. Matsueda Y. Imamura H. Hayase T. Morioka H. Tabira H. Yamamoto J. Kowata Y. Tetrahedron Asymmetry 14 2003 185
57. Sato I. Urabe H. Ishiguro S. Shibata T. Soai K. Angew. Chem. Int. Ed. 42 2003 315
58. Ueoka R. Matsumoto Y. Nagamatsu T. Hirohata S. Chem. Lett. 1984 583
59. Borszéky K. Mallat T. Aeschiman R. Schiweizer W.B. Baiker A. J. Catal. 161 1996 451
60. Nishida T. Miyafuji A. Ito Y.N. Katsuki T. Tetrahedron Lett. 41 2000 7053
61. Girard C. Kagan H.B. Angew. Chem. Int. Ed. 37 1998 2922
62. von Kiedrowski G. in: Pályi G. Zucchi C. Caglioti L. (Eds.) Fundamentals of Life 2002 38 Elsevier Paris