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Volumn 65, Issue 8, 2000, Pages 2517-2527

Nondynamic kinetic resolution of configurationally stable biaryl lactones by reduction with oxazaborolidine-activated borane: AM1 studies and experimental verification

Author keywords

[No Author keywords available]

Indexed keywords

BORANE DERIVATIVE; LACTONE DERIVATIVE; OXAZABOROLIDINE DERIVATIVE;

EID: 0034697128     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991729x     Document Type: Article
Times cited : (40)

References (58)
  • 7
    • 0000718373 scopus 로고    scopus 로고
    • (b) Pu, L. Chem. Rev. 1998, 98, 2405.
    • (1998) Chem. Rev. , vol.98 , pp. 2405
    • Pu, L.1
  • 32
  • 34
    • 0343611983 scopus 로고    scopus 로고
    • note
    • The main goal of this study is an improved understanding of the mechanistic course of the reaction and to find out which step is decisive for the experimentally observed selectivity. For the calculation of the relative rate constant and the enantiomeric excess, the theoretical values were used with an accuracy of ±0.01 kcal/mol. It must be noted, however, that the error bars of AMI calculations are larger than that. Furthermore, the neglect of entropy effects leads to an additional uncertainty of more than 0.01 kcal/mol.
  • 35
    • 0342306984 scopus 로고    scopus 로고
    • note
    • 28 in which some approximations (e.g., the corresponding entropy parts of reactions with similar activation enthalpies are supposed to be equal; consequently, these entropy terms can be neglected) had to be made. Formula Presented
  • 39
    • 0343611981 scopus 로고    scopus 로고
    • note
    • rel would decrease to 2.13 (corresponding to a ratio (M)-9:(P)-9 = 68:32), hence still predicting the qualitatively right (M)-selectivity.
  • 43
    • 0033975522 scopus 로고    scopus 로고
    • (P)-6f had previously been obtained by ring opening of racemic 6f with chiral O-nucleophiles, atropo-diastereomeric resolution, followed by saponification of the stereo-pure esters and subsequent recyclization, though in moderate yields and not fully enantiomerically pure. See: Bringmann, G.; Heubes, M.; Breuning, M.; Göbel, L.; Ochse, M.; Schöner, B., Schupp, O. J. Org. Chem., 2000, 65, 722.
    • (2000) J. Org. Chem. , vol.65 , pp. 722
    • Bringmann, G.1    Heubes, M.2    Breuning, M.3    Göbel, L.4    Ochse, M.5    Schöner, B.6    Schupp, O.7
  • 44
    • 0343611980 scopus 로고    scopus 로고
    • note
    • rel = 26), still with a preferential reduction of (M)-6f.
  • 48
    • 0001499101 scopus 로고    scopus 로고
    • Under different reaction conditions, the kinetic resolution of racemic 14 with 1.1 equiv of (S)-4 and with catechol borane as the reductant (2.0 equiv in toluene or 0.2 equiv in THF) gave weak preferences in favor of (P)-7f (er 60:40 and 77:23, respectively) at < 20% conversion (20 °C), see: Bringmann, G.; Breuning, M. Synlett 1998, 634.
    • (1998) Synlett , pp. 634
    • Bringmann, G.1    Breuning, M.2
  • 49
    • 37049047699 scopus 로고
    • For the nonstereoselective preparation of related 1-(2′-tertbutylphenyl)naphthalenes, see i.a. Lesslie, M. S.; Mayer, U. J. H. J. Chem. Soc. 1962, 1401.
    • (1962) J. Chem. Soc. , pp. 1401
    • Lesslie, M.S.1    Mayer, U.J.H.2
  • 51
    • 0004321724 scopus 로고    scopus 로고
    • available from Oxford Molecular Ltd., The Magdalen Centre, Oxford Science Park, Sandford-on-Thames, Oxford 0X4 4GA, England
    • Rauhut, G.; Chandrasekhar, J.; Alex, A.; Beck, B.; Sauer, W.; Clark, T. VAMP 6.1, available from Oxford Molecular Ltd., The Magdalen Centre, Oxford Science Park, Sandford-on-Thames, Oxford 0X4 4GA, England.
    • VAMP 6.1
    • Rauhut, G.1    Chandrasekhar, J.2    Alex, A.3    Beck, B.4    Sauer, W.5    Clark, T.6
  • 52
    • 0342742034 scopus 로고    scopus 로고
    • Tripos Associates, 1699 St. Hanley Road, Suite 303, St. Louis, MO, 63144
    • SYBYL; Tripos Associates, 1699 St. Hanley Road, Suite 303, St. Louis, MO, 63144.
    • SYBYL
  • 56
    • 0343176495 scopus 로고    scopus 로고
    • note
    • It is necessary to use 12 in analytically pure form.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.