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Volumn 11, Issue 19, 2005, Pages 5509-5522

The prediction of the absolute stereochemistry of primary and secondary 1,2-diols by1H NMR spectroscopy: Principles and applications

Author keywords

Chirality; Configuration determination; Methoxyphenylacetic acid; NMR spectroscopy; Stereochemistry

Indexed keywords

CARBON; ESTERS; GRAPH THEORY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 25444502911     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200500181     Document Type: Article
Times cited : (35)

References (44)
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    • Determination of the absolute configuration of biologically active compounds by the modified mosher's method
    • (Eds.: R. Cooper, J. K. Snyder), Dekker, New York
    • g) "Determination of the Absolute Configuration of Biologically Active Compounds by the Modified Mosher's Method": T. Kusumi, I. Ohtani in The Biology-Chemistry Interface (Eds.: R. Cooper, J. K. Snyder), Dekker, New York, 1999, pp. 103-137;
    • (1999) The Biology-chemistry Interface , pp. 103-137
    • Kusumi, T.1    Ohtani, I.2
  • 11
    • 25444494833 scopus 로고    scopus 로고
    • note
    • RS values and calculated as the difference between the chemical shift in the (S)- and (R)-MTPA derivatives.
  • 17
    • 0000002768 scopus 로고
    • Nuclear magnetic resonance analysis using chiral derivatives
    • (Ed.: J. D. Morrison), Academic Press, New York
    • c) "Nuclear Magnetic Resonance Analysis Using Chiral Derivatives": S. Yamaguchi in Asymmetric Synthesis, Vol. 1 (Ed.: J. D. Morrison), Academic Press, New York, 1983, pp. 125-152;
    • (1983) Asymmetric Synthesis , vol.1 , pp. 125-152
    • Yamaguchi, S.1
  • 18
    • 0000523834 scopus 로고    scopus 로고
    • (Eds.: G. Helchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, New York
    • d) G. Uray in Houben-Weyl Methods in Organic Chemistry, Vol. 1 (Eds.: G. Helchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, New York, 1996, p. 253;
    • (1996) Houben-Weyl Methods in Organic Chemistry , vol.1 , pp. 253
    • Uray, G.1
  • 20
    • 0000237404 scopus 로고
    • f) D. Parker, Chem. Rev. 1991, 91, 1441-1457.
    • (1991) Chem. Rev. , vol.91 , pp. 1441-1457
    • Parker, D.1
  • 35
    • 25444497842 scopus 로고    scopus 로고
    • note
    • a) J(H(1′),H(2′)) and δ of methylene protons for bis-(R)-MPA ester of (S)-1,2-propanediol: 3.2 Hz and 4.2 ppm for pro-S-H(1′) and 6.9 Hz and 3.9 ppm for pro-R-H(1′), respectively;
  • 36
    • 25444451704 scopus 로고    scopus 로고
    • note
    • b) J(H(1′),H(2′)) and δ of methylene protons for bis-(S)-MPA ester of (S)-propane-1,2-diol: 3.5 Hz and 4.2 ppm for pra-S-H(1′) and 6.5 Hz and 4.1 ppm for pro-R-H(1′)-pro-R, respectively.
  • 42
    • 25444502726 scopus 로고    scopus 로고
    • note
    • From the NMR point of view in the bis-(R)-MPA esters conformers sp-I and sp-II are practically identical, the only difference is the slightly different orientation in the carbonyl group (±30°).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.