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Volumn , Issue 2, 2008, Pages 229-236

Enantioselective synthesis of 2-substituted alcohols using (+)-(1S,2S)-pseudoephedrine as chiral auxiliary

Author keywords

Alcohols; Alkylation; Asymmetric synthesis; Auxiliary; Reduction

Indexed keywords

ASYMMETRIC SYNTHESIS; EPIMERIZATION; HYDROXYL GROUPS; REDUCTIVE CLEAVAGE;

EID: 38849133490     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1000851     Document Type: Article
Times cited : (12)

References (37)
  • 9
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    • Frater, G. In Houben- Weyl, 4th ed., E21; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart, 1996, 723.
    • (a) Frater, G. In Houben- Weyl, 4th ed., Vol. E21; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart, 1996, 723.
  • 10
    • 38849203315 scopus 로고    scopus 로고
    • Högberg, H.-E. In Houben-Weyl, 4th ed., E21; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart, 1996, 791.
    • (b) Högberg, H.-E. In Houben-Weyl, 4th ed., Vol. E21; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart, 1996, 791.
  • 11
    • 0002782655 scopus 로고
    • Trost, B. M, Fleming, I, Eds, Pergamon Press: Oxford, Chap. 1.1
    • (c) Caine, D. In Comprehensive Organic Synthesis, Vol. 3; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, Chap. 1.1.
    • (1991) Comprehensive Organic Synthesis , vol.3
    • Caine, D.1
  • 12
    • 38849187389 scopus 로고    scopus 로고
    • Norin, T. In Houben-Weyl, 4th ed., E21; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart, 1996, 697.
    • (d) Norin, T. In Houben-Weyl, 4th ed., Vol. E21; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart, 1996, 697.
  • 20
    • 38849142749 scopus 로고    scopus 로고
    • Fey, P. In Houben-Weyl, 4th ed., E21; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart, 1996, 973.
    • (a) Fey, P. In Houben-Weyl, 4th ed., Vol. E21; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart, 1996, 973.
  • 21
    • 38849188083 scopus 로고    scopus 로고
    • Fey, P. In Houben-Weyl, 4th ed., E21; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart, 1996, 994.
    • (b) Fey, P. In Houben-Weyl, 4th ed., Vol. E21; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart, 1996, 994.
  • 24
    • 38849084769 scopus 로고    scopus 로고
    • The desired S-configuration for alcohol 5a originates in the alkylation reaction. According to Myers,4b the newly introduced alkyl chain is attached from the side which comprises the methyl substituent of the pseudoephedrine side chain. We measured the optical rotation for (S)-5a to be [α]D20-11.8 (c 1.00, CHCl3, In the literature the value for the enantiomer (R)-5a was published as [α]D24+9.04 (c 1.2, CHCl3).15 The opposite signs illustrate that these compounds are enantiomers and the higher value for our compound is due to its higher optical purity. Additionally, the absolute configuration of the oxoamide precursor, 2S),1′S)-6a, which was converted into alcohol (S)-5a, was determined by X-ray diffraction.11
    • 11
  • 25
    • 38849163751 scopus 로고    scopus 로고
    • 4.
    • 4.
  • 26
    • 38849133721 scopus 로고    scopus 로고
    • 2O. Daicel Chiralpak® IA columns (n-hexane-2-propanol, 99:1) were used for the analytical and semi-preparative HPLC separation.
    • 2O. Daicel Chiralpak® IA columns (n-hexane-2-propanol, 99:1) were used for the analytical and semi-preparative HPLC separation.
  • 27
    • 38849090888 scopus 로고    scopus 로고
    • 2) columns. Epimeric mixtures of the hydroxyamides were used as standards; they were synthesized from racemic 2-substituted carboxylic acids, activated as acid chlorides, and reacted with (+)-(1S,2S)-pseudoephedrine.
    • 2) columns. Epimeric mixtures of the hydroxyamides were used as standards; they were synthesized from racemic 2-substituted carboxylic acids, activated as acid chlorides, and reacted with (+)-(1S,2S)-pseudoephedrine.
  • 28
    • 38849184826 scopus 로고    scopus 로고
    • Yields for the alkylation correspond to those published in the experimental section. The yields for the reduction of hydroxyamides 4a-f directly to the alcohols originate in unpublished results (L. F. Tietze, C. Raith).
    • Yields for the alkylation correspond to those published in the experimental section. The yields for the reduction of hydroxyamides 4a-f directly to the alcohols originate in unpublished results (L. F. Tietze, C. Raith).
  • 31
    • 38849191948 scopus 로고    scopus 로고
    • 13 All non-hydrogen atoms were refined anisotropically. All hydrogen atoms were included in the model. CCDC-664393 [(-)-(2S,1′S)-6a] contains the supplementary crystallographic data for this article. These data can be obtained free of charge from The Cambridge Cyrstallographic Data Centre via www.ccdc.ac.uk/data_request/cif.
    • 13 All non-hydrogen atoms were refined anisotropically. All hydrogen atoms were included in the model. CCDC-664393 [(-)-(2S,1′S)-6a] contains the supplementary crystallographic data for this article. These data can be obtained free of charge from The Cambridge Cyrstallographic Data Centre via www.ccdc.ac.uk/data_request/cif.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.