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Volumn 12, Issue 21, 2010, Pages 4800-4803

Pyridylalanine (Pal)-peptide catalyzed enantioselective allenoate additions to N-acyl imines proceed via an atypical "aza-Morita-Baylis-Hillman" mechanism

Author keywords

[No Author keywords available]

Indexed keywords

ALANINE; HETEROCYCLIC COMPOUND; IMINE; PEPTIDE; PYRIDINE; PYRIDINE DERIVATIVE;

EID: 78049525548     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101947s     Document Type: Article
Times cited : (23)

References (25)
  • 2
    • 78049487193 scopus 로고    scopus 로고
    • For a report on the DABCO catalyzed coupling of allenoates with N -Boc imines, see
    • For a report on the DABCO catalyzed coupling of allenoates with N -Boc imines, see
  • 4
    • 59649098742 scopus 로고    scopus 로고
    • For reviews on the aza-MBH reaction, see
    • For reviews on the aza-MBH reaction, see: Declerck, V.; Martinez, J.; Lamaty, F. Chem. Rev 2009, 109, 1
    • (2009) Chem. Rev , vol.109 , pp. 1
    • Declerck, V.1    Martinez, J.2    Lamaty, F.3
  • 9
    • 78049520045 scopus 로고    scopus 로고
    • For a review, see
    • For a review, see
  • 16
    • 78049487389 scopus 로고    scopus 로고
    • In the presence of protic additives, the reaction becomes first order in aldehyde. See refs 6d and 6e
    • In the presence of protic additives, the reaction becomes first order in aldehyde. See refs 6d and 6e.
  • 19
    • 78049500277 scopus 로고    scopus 로고
    • For reaction rate plots at the various concentrations, see Supporting Information
    • For reaction rate plots at the various concentrations, see Supporting Information.
  • 20
    • 78049519488 scopus 로고    scopus 로고
    • The imine concentration was not raised above 0.15 M due to its insolubility in toluene at higher concentrations. The slightly lower value of the rate constant at 0.15 M may be due to solubility issues
    • The imine concentration was not raised above 0.15 M due to its insolubility in toluene at higher concentrations. The slightly lower value of the rate constant at 0.15 M may be due to solubility issues.
  • 21
    • 78049500690 scopus 로고    scopus 로고
    • The following case exhibits similar kinetics, in the presence of protic additives. See
    • The following case exhibits similar kinetics, in the presence of protic additives. See
  • 23
    • 78049497729 scopus 로고    scopus 로고
    • For individual reaction rate plots for each trial and the procedure for the preparation of allenoate 2a-D, see Supporting Information
    • For individual reaction rate plots for each trial and the procedure for the preparation of allenoate 2a-D, see Supporting Information.
  • 24
    • 78049517555 scopus 로고    scopus 로고
    • For a discussion of related P-initiated zwitterions, see
    • For a discussion of related P-initiated zwitterions, see


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.