메뉴 건너뛰기




Volumn , Issue 7, 2008, Pages 1253-1264

Resolution of racemic N-benzyl α-amino acids by liquid-liquid extraction: A practical method using a lipophilic chiral cobalt(III) salen complex and mechanistic studies

Author keywords

Amino acids; Cobalt; Recognition; Resolution; Salen ligands

Indexed keywords


EID: 53549083007     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200701101     Document Type: Article
Times cited : (38)

References (82)
  • 12
    • 0033006463 scopus 로고    scopus 로고
    • and references cited therein;
    • d) T. Miyzawa, Amino Acids 1999, 16, 191-213, and references cited therein;
    • (1999) Amino Acids , vol.16 , pp. 191-213
    • Miyzawa, T.1
  • 13
    • 0041152088 scopus 로고    scopus 로고
    • and references cited therein;
    • e) G. Carrea, S. Riva, Angew. Chem. Int. Ed. 2000, 39, 2226-2254, and references cited therein;
    • (2000) Angew. Chem. Int. Ed , vol.39 , pp. 2226-2254
    • Carrea, G.1    Riva, S.2
  • 15
    • 0035847187 scopus 로고    scopus 로고
    • For an excellent review covering simulated moving bed (SMB) chromatography and applications of SMB to the separation of enantiomers, see: M. Schulte, J. Strube, J. Chromatogr. A 2001, 906, 399-416, and references cited therein.
    • For an excellent review covering simulated moving bed (SMB) chromatography and applications of SMB to the separation of enantiomers, see: M. Schulte, J. Strube, J. Chromatogr. A 2001, 906, 399-416, and references cited therein.
  • 26
    • 53849137303 scopus 로고    scopus 로고
    • [6f]
    • [6f]
  • 27
    • 0042786588 scopus 로고    scopus 로고
    • and references cited therein;
    • a) P. D. Knight, P. Scott, Coord. Chem. Rev. 2003, 242, 125, and references cited therein;
    • (2003) Coord. Chem. Rev , vol.242 , pp. 125
    • Knight, P.D.1    Scott, P.2
  • 47
    • 53849115703 scopus 로고    scopus 로고
    • [14]).
    • [14]).
  • 50
    • 35348918846 scopus 로고    scopus 로고
    • 3-amino acids, see: P. Dzygiel, C. Monti, U. Piarulli, C. Gennari, Org. Biomol. Chem. 2007, 5, 3464-3471.
    • 3-amino acids, see: P. Dzygiel, C. Monti, U. Piarulli, C. Gennari, Org. Biomol. Chem. 2007, 5, 3464-3471.
  • 51
    • 0035437897 scopus 로고    scopus 로고
    • 4], see: I. L. Lysenko, O. G. Kulinkovich, Russ. J. Org. Chem. 2001, 37, 1238-1243;
    • 4], see: I. L. Lysenko, O. G. Kulinkovich, Russ. J. Org. Chem. 2001, 37, 1238-1243;
  • 52
    • 0034048903 scopus 로고    scopus 로고
    • for the preparation of enzyme inhibitors, see
    • b) for the preparation of enzyme inhibitors, see: C. T. Supuran, A. Scozzafava, Eur. J. Pharm. Sci. 2000, 10, 67-76;
    • (2000) Eur. J. Pharm. Sci , vol.10 , pp. 67-76
    • Supuran, C.T.1    Scozzafava, A.2
  • 53
    • 0030014025 scopus 로고    scopus 로고
    • for the synthesis of 2,3,4-trisubstituted piperidines, see
    • c) for the synthesis of 2,3,4-trisubstituted piperidines, see: S. Laschat, R. Fröhlich, B. Wibbeling, J. Org. Chem. 1996, 61, 2829-2838;
    • (1996) J. Org. Chem , vol.61 , pp. 2829-2838
    • Laschat, S.1    Fröhlich, R.2    Wibbeling, B.3
  • 54
    • 0034649135 scopus 로고    scopus 로고
    • for the synthesis of statine and hydroxymethylene dipeptide isosteres, see
    • d) for the synthesis of statine and hydroxymethylene dipeptide isosteres, see: A. McCluskey, J. Garner, D. J. Young, S. Caballero, Tetrahedron Lett. 2000, 41, 8147-8151.
    • (2000) Tetrahedron Lett , vol.41 , pp. 8147-8151
    • McCluskey, A.1    Garner, J.2    Young, D.J.3    Caballero, S.4
  • 60
    • 53849127845 scopus 로고    scopus 로고
    • The variation of other parameters (stirring speed, concentrations, type of reaction vessel) did not significantly affect the extraction results yields and enantioselectivities, Once the extraction was complete, the enantiomeric excesses did not vary over additional time
    • The variation of other parameters (stirring speed, concentrations, type of reaction vessel) did not significantly affect the extraction results (yields and enantioselectivities). Once the extraction was complete, the enantiomeric excesses did not vary over additional time.
  • 68
    • 35048842033 scopus 로고    scopus 로고
    • A similar enantiomeric exchange occurring at high temperatures and leading to the thermodynamically most stable complex was recently described in the case of a ruthenium complex [RuCl2(PP)NN, see: W. Baratta, G. Chelucci, E. Herdtweck, S. Magnolia, K. Siega, P. Rigo, Angew. Chem. Int. Ed. 2007, 46, 7651-7654
    • 2(PP)(NN)], see: W. Baratta, G. Chelucci, E. Herdtweck, S. Magnolia, K. Siega, P. Rigo, Angew. Chem. Int. Ed. 2007, 46, 7651-7654.
  • 75
    • 53849112958 scopus 로고    scopus 로고
    • HyperChem™ Professional 7.51, Hypercube, Inc., 1115 NW 4th Street, Gainesville, Florida 32601, USA.
    • HyperChem™ Professional 7.51, Hypercube, Inc., 1115 NW 4th Street, Gainesville, Florida 32601, USA.
  • 78
    • 0345491105 scopus 로고    scopus 로고
    • Becke's three-parameter hybrid method using the LYP (C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789)
    • Becke's three-parameter hybrid method using the LYP (C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789)
  • 79
    • 0000189651 scopus 로고    scopus 로고
    • correlation functional: A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
    • correlation functional: A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
  • 81
    • 53849090253 scopus 로고    scopus 로고
    • In the case of NOE contacts involving groups CH3, tBu, the shortest measured H-H distance is reported
    • 3, tBu), the shortest measured H-H distance is reported.
  • 82
    • 53849111896 scopus 로고    scopus 로고
    • Jaguar, version 6.0, Schrödinger, LLC, New York, NY, 2005
    • Jaguar, version 6.0, Schrödinger, LLC, New York, NY, 2005.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.