메뉴 건너뛰기




Volumn 126, Issue 22, 2004, Pages 6967-6971

Structure-selectivity relationships and structure for a peptide-based enantioselective acylation catalyst

Author keywords

[No Author keywords available]

Indexed keywords

ACYLATION; AMINO ACIDS; REACTION KINETICS; SOLUTIONS; STEREOCHEMISTRY; STRUCTURE (COMPOSITION);

EID: 3042721763     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja049661c     Document Type: Article
Times cited : (75)

References (34)
  • 1
    • 0003445429 scopus 로고    scopus 로고
    • Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin Heidelberg
    • Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin Heidelberg, 1999; Vols. I-III.
    • (1999) Comprehensive Asymmetric Catalysis , vol.1-3
  • 3
    • 0034750244 scopus 로고    scopus 로고
    • (b) List, B. Synlett 2001, 11, 1675-1686.
    • (2001) Synlett , vol.11 , pp. 1675-1686
    • List, B.1
  • 4
    • 0037043180 scopus 로고    scopus 로고
    • (c) List, B. Tetrahedron 2002, 58, 5573-5590.
    • (2002) Tetrahedron , vol.58 , pp. 5573-5590
    • List, B.1
  • 9
    • 3042699088 scopus 로고    scopus 로고
    • Asymmetric acylation
    • Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin Heidelberg; Chapter 43
    • (b) Jarvo, E. R.; Miller, S. J. "Asymmetric Acylation" In Comprehensive Asymmetric Catalysis, Supplement 1; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin Heidelberg, 2004; Chapter 43.
    • (2004) Comprehensive Asymmetric Catalysis, Supplement 1
    • Jarvo, E.R.1    Miller, S.J.2
  • 10
    • 0033921576 scopus 로고    scopus 로고
    • For other representative nonenzymatic catalysts that effect kinetic resolution of racemic alcohols by acylation, see: (a) Fu, G. C. Acc. Chem. Res. 2000, 33, 412-420.
    • (2000) Acc. Chem. Res. , vol.33 , pp. 412-420
    • Fu, G.C.1
  • 15
    • 85050296727 scopus 로고
    • rel) were calculated according to the method of Kagan. See: (a) Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249-330.
    • (1988) Top. Stereochem. , vol.18 , pp. 249-330
    • Kagan, H.B.1    Fiaud, J.C.2
  • 16
    • 3042736784 scopus 로고    scopus 로고
    • note
    • (b) Reaction selectivities and conversions were determined with the methods we reported previously (ref 3).
  • 19
    • 0002748457 scopus 로고
    • Nucleophilic versus general base catalysis with alkylimidazoles has been a subject of some debate. We have adopted the nucleophilic paradigm for the sterically unencumbered moiety for this analysis. (a) Guibe-Jampel, E.; Bram, G.; Vilkas, M. Bull. Soc. Chim. Fr. 1973, 1021-1027.
    • (1973) Bull. Soc. Chim. Fr. , pp. 1021-1027
    • Guibe-Jampel, E.1    Bram, G.2    Vilkas, M.3
  • 22
    • 3042815719 scopus 로고    scopus 로고
    • note
    • rel = 30 when 2.5 mol % peptide 1 is employed as the catalyst. For this substrate, extended reaction times (48-72 h) are required to achieve 40-50% conversion.
  • 23
    • 3042777450 scopus 로고    scopus 로고
    • note
    • A direct comparison of the catalytic performance of the peptide in chloroform is difficult due to the freezing of this reaction mixture at -65 °C.
  • 27
    • 3042731918 scopus 로고    scopus 로고
    • See Supporting Information for details
    • See Supporting Information for details.
  • 30
    • 3042815720 scopus 로고    scopus 로고
    • Available in Sybyl 6.9 (Tripos Software, St. Louis, MO.)
    • (a) Available in Sybyl 6.9 (Tripos Software, St. Louis, MO.)
  • 32
    • 3042735507 scopus 로고    scopus 로고
    • See ref 5e
    • See ref 5e.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.