메뉴 건너뛰기




Volumn 44, Issue 5, 2005, Pages 807-811

Highly efficient dynamic kinetic resolution of azlactones by urea-based bifunctional organocatalysts

Author keywords

Amino acids; Azlactones; Kinetic resolution; Organocatalysts; Urea

Indexed keywords

AMINO ACIDS; CATALYSTS; UREA;

EID: 13444270903     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200461442     Document Type: Article
Times cited : (265)

References (50)
  • 2
    • 1842578074 scopus 로고    scopus 로고
    • M. Breuer, K. Ditrich, T. Habicher, B. Hauer, M. Keßeler, R. Stürmer, T. Zelinski, Angew. Chem. 2004, 116, 806-843; Angew. Chem. Int. Ed. 2004, 43, 788-824.
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 788-824
  • 3
    • 0003993814 scopus 로고    scopus 로고
    • (Ed.: R. N. Patel), Marcel Dekker, New York
    • R. N. Patel in Stereoselective Biocatalysis (Ed.: R. N. Patel), Marcel Dekker, New York, 2000, pp. 877-902.
    • (2000) Stereoselective Biocatalysis , pp. 877-902
    • Patel, R.N.1
  • 10
    • 13444291232 scopus 로고    scopus 로고
    • note
    • a, value of the hydrogen atom at the 4-position is about 8.9.[9] Azlactones are racemized easily by external bases, but autocatalytic racemization can also occur.[10] See reference [11] for an example of the crystallization-induced generation of a diastereomerically pure azlactone.
  • 25
    • 0037165402 scopus 로고    scopus 로고
    • The catalytic activity of ureas through hydrogen bonding has been shown to be comparable to the action of metal-containing Lewis acids: P. R. Schreiner, A. Wittkopp, Org. Lett. 2002, 4, 217-220; A. Wittkopp, P. R. Schreiner, Chem. Eur. J. 2003, 9, 407-414; P. R. Schreiner, Chem. Soc. Rev. 2003, 32, 289-296.
    • (2002) Org. Lett. , vol.4 , pp. 217-220
    • Schreiner, P.R.1    Wittkopp, A.2
  • 26
    • 0037455338 scopus 로고    scopus 로고
    • The catalytic activity of ureas through hydrogen bonding has been shown to be comparable to the action of metal-containing Lewis acids: P. R. Schreiner, A. Wittkopp, Org. Lett. 2002, 4, 217-220; A. Wittkopp, P. R. Schreiner, Chem. Eur. J. 2003, 9, 407-414; P. R. Schreiner, Chem. Soc. Rev. 2003, 32, 289-296.
    • (2003) Chem. Eur. J. , vol.9 , pp. 407-414
    • Wittkopp, A.1    Schreiner, P.R.2
  • 27
    • 0346865819 scopus 로고    scopus 로고
    • The catalytic activity of ureas through hydrogen bonding has been shown to be comparable to the action of metal-containing Lewis acids: P. R. Schreiner, A. Wittkopp, Org. Lett. 2002, 4, 217-220; A. Wittkopp, P. R. Schreiner, Chem. Eur. J. 2003, 9, 407-414; P. R. Schreiner, Chem. Soc. Rev. 2003, 32, 289-296.
    • (2003) Chem. Soc. Rev. , vol.32 , pp. 289-296
    • Schreiner, P.R.1
  • 28
    • 9244238796 scopus 로고    scopus 로고
    • P. M. Pihko, Angew. Chem. 2004, 116, 2110-2113; Angew. Chem. Int. Ed. 2004, 43, 2062-2064.
    • (2004) Angew. Chem. , vol.116 , pp. 2110-2113
    • Pihko, P.M.1
  • 29
    • 4544221552 scopus 로고    scopus 로고
    • P. M. Pihko, Angew. Chem. 2004, 116, 2110-2113; Angew. Chem. Int. Ed. 2004, 43, 2062-2064.
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 2062-2064
  • 30
    • 0000714570 scopus 로고    scopus 로고
    • For seminal studies on the use of chiral amidinium catalysts for stereoselective Diels-Alder reactions, see: T. Schuster, M. Bauch, G. Dürner, M. W. Göbel, Org. Lett. 2000, 2, 179-181; T. Schuster, M. Kurz, M. W. Göbel, J. Org. Chem. 2000, 65, 1697-1701.
    • (2000) Org. Lett. , vol.2 , pp. 179-181
    • Schuster, T.1    Bauch, M.2    Dürner, G.3    Göbel, M.W.4
  • 31
    • 0034708422 scopus 로고    scopus 로고
    • For seminal studies on the use of chiral amidinium catalysts for stereoselective Diels-Alder reactions, see: T. Schuster, M. Bauch, G. Dürner, M. W. Göbel, Org. Lett. 2000, 2, 179-181; T. Schuster, M. Kurz, M. W. Göbel, J. Org. Chem. 2000, 65, 1697-1701.
    • (2000) J. Org. Chem. , vol.65 , pp. 1697-1701
    • Schuster, T.1    Kurz, M.2    Göbel, M.W.3
  • 32
    • 13444273117 scopus 로고    scopus 로고
    • note
    • The synthesis and full characterization of the bifunctional catalysts 1a,c-g, 2, 3a,b, 4, 5a,b, 6, and 7 will be published elsewhere.
  • 33
    • 0004150157 scopus 로고    scopus 로고
    • University of Göttingen, Germany
    • Kα radiation (γ = 0.71073 Å), graphite monochromator, φ/ω scans. The structure was solved by using direct methods (G. M. Sheldrick, SHELXS-97, Program for the Solution of Crystal Structures, University of Göttingen, Germany, 1997), followed by full-matrix least-squares refinement (by using all unique reflections) with anisotropic thermal parameters for non-hydrogen atoms. The positions of hydrogen atoms were refined by using a riding model (SHELXL-97). CCDC 246910 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
    • (1997) SHELXS-97, Program for the Solution of Crystal Structures
    • Sheldrick, G.M.1
  • 34
    • 13444270522 scopus 로고    scopus 로고
    • Kα radiation (γ = 0.71073 Å), graphite monochromator, φ/ω scans. The structure was solved by using direct methods (G. M. Sheldrick, SHELXS-97, Program for the Solution of Crystal Structures, University of Göttingen, Germany, 1997), followed by full-matrix least-squares refinement (by using all unique reflections) with anisotropic thermal parameters for non-hydrogen atoms. The positions of hydrogen atoms were refined by using a riding model (SHELXL-97). CCDC 246910 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
  • 35
    • 33845278631 scopus 로고
    • For the solid-state structural features and the typical bifurcate H bonding of ureas to nucleophilic O acceptors, see: M. C. Etter, T. W. Panunto, J. Am. Chem. Soc. 1988, 110, 5896-5897; M. C. Etter, Acc. Chem. Res. 1990, 23, 120-126.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 5896-5897
    • Etter, M.C.1    Panunto, T.W.2
  • 36
    • 0006589268 scopus 로고
    • For the solid-state structural features and the typical bifurcate H bonding of ureas to nucleophilic O acceptors, see: M. C. Etter, T. W. Panunto, J. Am. Chem. Soc. 1988, 110, 5896-5897; M. C. Etter, Acc. Chem. Res. 1990, 23, 120-126.
    • (1990) Acc. Chem. Res. , vol.23 , pp. 120-126
    • Etter, M.C.1
  • 37
    • 13444278666 scopus 로고    scopus 로고
    • note
    • The urea catalyst 1a did not show a comparable increase in enantioselectivity with decreasing temperature: At 0°C the product 9e was formed with 88% ee (87% ee at room temperature; Table 1, entry 5).
  • 38
    • 13444306320 scopus 로고    scopus 로고
    • note
    • In the HPLC analysis (see Experimental Section) of the racemic azlactones 8a-f on a chiral stationary phase, equilibration of the azlactone enantiomers was clearly indicated by the peak forms typical for dynamic, interconverting analytes (see, for example. reference [30]).
  • 41
    • 13444309257 scopus 로고    scopus 로고
    • note
    • The synthesis and characterization of the diureas 11 and 12 will be reported elsewhere.
  • 43
    • 13444292039 scopus 로고    scopus 로고
    • note
    • 2AQN: dihydroquinidine-(anthraquinone-1,4-diyl diether).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.