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Volumn 65, Issue 9, 2000, Pages 2658-2666

Assignment of the absolute configuration of α-chiral carboxylic acids by 1H NMR spectroscopy

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE;

EID: 0034607851     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9916838     Document Type: Article
Times cited : (50)

References (52)
  • 1
    • 84899775201 scopus 로고    scopus 로고
    • Helmchen, G. R., Hoffmann, W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, New York
    • For a review on the use of NMR for assignment of absolute configuration and ee measurements, see: Uray, G. Houben-Weyl: Methods in Organic Chemistry; Helmchen, G. R., Hoffmann, W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, New York, 1996; Vol. 1, p 253.
    • (1996) Methods in Organic Chemistry , vol.1 , pp. 253
    • Houben-Weyl, U.G.1
  • 13
    • 84899778889 scopus 로고    scopus 로고
    • note
    • α-OMe and C=O groups, respectively. See ref 2c
  • 14
    • 84899779828 scopus 로고    scopus 로고
    • note
    • RS = δR - δS).
  • 36
    • 49249150528 scopus 로고
    • Ring current theories in NMR
    • Pergamon Press: Elmsford, NY
    • (f) Haigh, C. W.; Mallion, R. B. Ring current theories in NMR. In Progress in NMR spectroscopy; Pergamon Press: Elmsford, NY, 1980; pp 303-344.
    • (1980) Progress in NMR Spectroscopy , pp. 303-344
    • Haigh, C.W.1    Mallion, R.B.2
  • 38
    • 84899782272 scopus 로고    scopus 로고
    • note
    • (a) For the (R)-9-AHA ester of 6: DE = 0.93 (AM1), 0.93 (PM3).
  • 39
    • 84899778474 scopus 로고    scopus 로고
    • note
    • (b) For the (S)-9-AHA ester of 6: DE = 0.48 (AM1), 0.39 (PM3).
  • 40
    • 84899777368 scopus 로고    scopus 로고
    • note
    • 2 in the systematic name. In those works, the sp conformer was defined by the synperiplanar disposition of the CαOMe and C=O groups.
  • 41
    • 84899771128 scopus 로고    scopus 로고
    • note
    • 2)].
  • 42
    • 84899783204 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra was observed at ca. T = 243 K. Only data for the major form are given in the table. Assignment of the minor component is ambiguous because of its very low population.
  • 44
    • 84899778256 scopus 로고    scopus 로고
    • note
    • 1H NMR data of the NHBoc group are very sensitive to experimental conditions and should not be used to derive the configuration (see ref 2h).
  • 45
    • 84899773246 scopus 로고    scopus 로고
    • note
    • 4 in MeOH.
  • 46
    • 0029145724 scopus 로고
    • Transformation of the trans-alcohol (41) into the diastereomeric cis-alcohol (42) was carried out by the Mitsunobu reaction; see: Takahashi, M.; Ogasawara, K. Tetrahedron: Asymmetry 1995, 6, 1617-1620.
    • (1995) Tetrahedron: Asymmetry , vol.6 , pp. 1617-1620
    • Takahashi, M.1    Ogasawara, K.2
  • 47
    • 84899782619 scopus 로고    scopus 로고
    • note
    • RS represents the difference between its chemical shift in the (1R,2S)-derivative and that in the (1S,2R)-derivative.
  • 49
    • 0030793714 scopus 로고    scopus 로고
    • RS values of the esters 19e, 12f, 19f, 12g, and 19g were measured after HPLC separation, whereas those of 6e, 12e, 6f, and 6g were directly measured from the spectra of the corresponding mixture.
    • (1997) Tetrahedron , vol.53 , pp. 10699-10708
    • Mizuno, M.1    Kanai, M.2    Iida, A.3    Tomioka, K.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.