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Volumn 127, Issue 4-5 SPEC. ISS., 2006, Pages 597-603

Self-disproportionation of enantiomers of (R)-ethyl 3-(3,5-dinitrobenzamido)-4,4,4-trifluorobutanoate on achiral silica gel stationary phase

Author keywords

Amino acids and derivatives; Achiral phase chromatography; Chirality; Fluorine and compounds; Self disproportionation of enantiomers; Separations

Indexed keywords


EID: 33745192709     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2005.11.004     Document Type: Article
Times cited : (104)

References (62)
  • 1
    • 33747613399 scopus 로고    scopus 로고
    • An example: formation of diastereomers using a covalent bond. In this case almost any available techniques can be used, such as fractional crystallization, distillation, sublimation or chromatography. See for instance:
  • 4
    • 0004219526 scopus 로고
    • Collins A.N., Sheldrake G.N., and Crosby J. (Eds), Wiley, New York
    • In: Collins A.N., Sheldrake G.N., and Crosby J. (Eds). Chirality in Industry (1992), Wiley, New York
    • (1992) Chirality in Industry
  • 5
    • 0003807713 scopus 로고    scopus 로고
    • Ahuja S. (Ed), American Chemical Society, Washington, DC
    • In: Ahuja S. (Ed). Chiral Separations, Applications and Technology (1997), American Chemical Society, Washington, DC
    • (1997) Chiral Separations, Applications and Technology
  • 6
    • 0003846223 scopus 로고    scopus 로고
    • Subramanian G. (Ed), Wiley-VCH, Weinheim
    • In: Subramanian G. (Ed). Chiral Separation Techniques (2001), Wiley-VCH, Weinheim
    • (2001) Chiral Separation Techniques
  • 9
    • 85055171459 scopus 로고    scopus 로고
    • An example: formation of diastereomers using strong electrostatic interactions as found in salts of chiral amines and acids. With some exceptions, the application of this approach is limited to fractional crystallization of diastereomeric salts. See for example:. Kozma D. (Ed), CRC Press, Boca Raton, FL
    • An example: formation of diastereomers using strong electrostatic interactions as found in salts of chiral amines and acids. With some exceptions, the application of this approach is limited to fractional crystallization of diastereomeric salts. See for example:. In: Kozma D. (Ed). CRC Handbook of Optical Resolutions via Diastereomeric Salt Formation (2001), CRC Press, Boca Raton, FL
    • (2001) CRC Handbook of Optical Resolutions via Diastereomeric Salt Formation
  • 10
    • 33747591066 scopus 로고    scopus 로고
    • note
    • An example: formation of diastereomers using hydrogen bonding or weak/medium electrostatic interactions. Successful application of this approach for separation of enantiomers requires amplification (number of interactions) of these weak diastereomeric relationships, which can be achieved using HPLC of GC conditions. For references see: Ref. [1].
  • 27
    • 33747602179 scopus 로고    scopus 로고
    • note
    • One of potential practical applications of this phenomenon might be the development of conceptually new and very economically efficient separation techniques.
  • 42
    • 33747603756 scopus 로고    scopus 로고
    • For instance, in the most recent book (a) and review article (b) on non-conventional methods for resolution of enantiomers, this phenomenon not even mentioned:
  • 45
    • 33747586598 scopus 로고    scopus 로고
    • note
    • The following definitions are found in the literature: "self-amplification of optical activity", "enantiomer-differentiation", "autoseparation of enantiomers", "separation of excess enantiomer", "enantiomeric enrichment" and "optical purification".
  • 55
    • 33747607342 scopus 로고    scopus 로고
    • note
    • The initial observation of poor reproducibility in the ee's and therefore the phenomenon of self-disproportionation of enantiomers was noticed in 1995. when we discovered highly enantioselective DBU-catalyzed 1,3-PSR. However, at that time the problem was solved by using Schiff base 4 for direct determination of its enantiomeric purity.
  • 56
    • 33747599467 scopus 로고    scopus 로고
    • note
    • In three previous examples (see Ref. [19]) of self-disproportionation of enantiomers on achiral silica gel, the highest Δ% ee difference between the lowest and the highest % ee obtained, were: 83% (Ref. [19a]), 31% (Ref. [19b]), and 21% (Ref. [19c]).
  • 62
    • 0030558966 scopus 로고    scopus 로고
    • Taking into account a report by Katagiri et al. on strong enantiomer self-disproportionation of isopropyl 3,3,3-trifluoro-2-hydroxypropanoate during distillation, one may envision that amplification of this phenomenon by a trifluoromethyl group may be of much general nature and other achiral methods available for separation of organic compounds can be applied. In particular, our next goal will be studying the enantiomer self-disproportionation of various trifluoromethyl-containing compounds under sublimation conditions. For Katagiri's original publication, see:
    • Taking into account a report by Katagiri et al. on strong enantiomer self-disproportionation of isopropyl 3,3,3-trifluoro-2-hydroxypropanoate during distillation, one may envision that amplification of this phenomenon by a trifluoromethyl group may be of much general nature and other achiral methods available for separation of organic compounds can be applied. In particular, our next goal will be studying the enantiomer self-disproportionation of various trifluoromethyl-containing compounds under sublimation conditions. For Katagiri's original publication, see:. Katagiri T., Yoda C., Furuhashi K., Ueki K., Kubota T. Chem. Lett. 2 (1996) 115-116
    • (1996) Chem. Lett. , vol.2 , pp. 115-116
    • Katagiri, T.1    Yoda, C.2    Furuhashi, K.3    Ueki, K.4    Kubota, T.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.