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Volumn 16, Issue 1, 2010, Pages 167-172

Kinetic resolution of the racemic 2-hydroxyalkanoates using the enantioselective mixed-anhydride method with pivalic anhydride and a chiral acyl-transfer catalyst

Author keywords

Anhydrides; Chirality; Density functional calculations; Enantioselectivity; Kinetic resolution

Indexed keywords

CARBOXYLIC ANHYDRIDE; COUPLING REAGENTS; DENSITY-FUNCTIONAL CALCULATIONS; DFT CALCULATION; ENANTIOSELECTIVE; KINETIC RESOLUTION; OPTICALLY ACTIVE; PIVALIC ANHYDRIDE; RACEMIC MIXTURES; RACEMIC SECONDARY ALCOHOLS; SEC-PHENETHYL ALCOHOL; STRUCTURAL FEATURE; TRANSITION STATE;

EID: 73949104105     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200902257     Document Type: Article
Times cited : (82)

References (37)
  • 1
    • 0000366453 scopus 로고
    • Enzymatic resolution of (R)- and (S)-hydroxylesters, see: a) T. Sugai, H. Ohta, Agrie. Biol. Chem. 1990, 54, 3337;
    • (1990) Agrie. Biol. Chem. , vol.54 , pp. 3337
    • Sugai, T.1    Ohta, H.2
  • 11
    • 3042699088 scopus 로고    scopus 로고
    • Asymmetric acylation
    • Eds. : E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer, Berlin, Chapter 43
    • i) "Asymmetric Acylation": E. R. Jarvo, S. J. Miller in Comprehensive Asymmetric Catalysis, Supplement 1 (Eds. : E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 2004, Chapter 43;
    • (2004) Comprehensive Asymmetric Catalysis, Supplement 1
    • Jarvo, E.R.1    Miller, S.J.2
  • 32
    • 73949102462 scopus 로고    scopus 로고
    • 1H NMR integration of the crude reaction mixture.
    • 1H NMR integration of the crude reaction mixture.
  • 33
    • 73949093834 scopus 로고    scopus 로고
    • A similar solvent effect was observed in the present study for the reaction of racemic benzyl lactate ((±)-1) with propionic anhydride as shown below. Chemical equation presented
    • A similar solvent effect was observed in the present study for the reaction of racemic benzyl lactate ((±)-1) with propionic anhydride as shown below. Chemical equation presented
  • 35
    • 73949093195 scopus 로고    scopus 로고
    • All calculations were performed with the program package Spartan '08 1.1.1 of Wavefunction Inc.
    • All calculations were performed with the program package Spartan '08 1.1.1 of Wavefunction Inc. (http://www.wavefun.com).
  • 36
    • 73949086853 scopus 로고    scopus 로고
    • Cartesian coordinates and absolute energies for all reported structures are included in the Supporting Information.
    • Cartesian coordinates and absolute energies for all reported structures are included in the Supporting Information.
  • 37
    • 73949106364 scopus 로고    scopus 로고
    • -1). Cartesian coordinates of the second stable transition state (S)-8-ts-2 to afford (S)-9 are described in the Supporting Information.
    • -1). Cartesian coordinates of the second stable transition state (S)-8-ts-2 to afford (S)-9 are described in the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.