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Volumn 17, Issue 4, 2006, Pages 620-633

Asymmetric synthesis of chiral bisoxazolines and their use as ligands in metal catalysis

Author keywords

[No Author keywords available]

Indexed keywords

ACID ANHYDRIDE; LIGAND; METAL; OXAZOLINE DERIVATIVE;

EID: 33645892914     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.12.036     Document Type: Article
Times cited : (31)

References (71)
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    • Reviews:
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    • (1991) Angew. Chem. , vol.103 , pp. 556-558
    • Bolm, C.1
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    • Schiffers, I. Ph.D. Dissertation, RWTH Aachen University, 2002.
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    • note
    • The enantioselective methanolysis was carried out in the presence of quinine, affording hemiester ent-9. Selective epimerization and saponification provided the corresponding trans (1S,2S)-diacid ent-11 in 72% yield.
  • 36
    • 33645851493 scopus 로고    scopus 로고
    • note
    • 2 + 20% THF). The mixture was then cooled to -15 °C and a solution of EEDQ was added via syringe. The reaction was stirred at rt for 48 h, the solvent and ethanol byproduct were removed in vacuum and the crude mixture was purified by column chromatography, yielding the desired product in 82% yield in analytically and diastereomerically pure form. Extension of the reaction time to 120 h resulted in a slight increase in the reaction yield (86% vs 82%). In a third approach, the EEDQ was added as a solid to a cooled solution (0 °C) of the two reactants in THF. The mixture was allowed to warm to rt and stirred for 120 h. The product was purified as previously described and isolated in 88% yield (1.0 mmol scale). After this preliminary investigation, the latter version seemed to be more suitable since the reaction was easier to perform compared to the first approaches.
  • 46
    • 0000097153 scopus 로고    scopus 로고
    • For a general overview on the Lewis acid catalyzed Diels-Alder reaction see:. Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds), Springer, Berlin
    • For a general overview on the Lewis acid catalyzed Diels-Alder reaction see:. Evans D.A., and Johnson J.S. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis Vol. 3 (1999), Springer, Berlin 1177-1236
    • (1999) Comprehensive Asymmetric Catalysis , vol.3 , pp. 1177-1236
    • Evans, D.A.1    Johnson, J.S.2
  • 47
    • 0000085376 scopus 로고    scopus 로고
    • For a general overview on the Lewis acid catalyzed hetero-Diels-Alder reaction see:. Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds), Springer, Berlin
    • For a general overview on the Lewis acid catalyzed hetero-Diels-Alder reaction see:. Ooi T., and Maruoka K. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis Vol. 3 (1999), Springer, Berlin 1237-1254
    • (1999) Comprehensive Asymmetric Catalysis , vol.3 , pp. 1237-1254
    • Ooi, T.1    Maruoka, K.2
  • 52
    • 0001403071 scopus 로고    scopus 로고
    • Reviews:. Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds), Springer, Berlin
    • Reviews:. Pfaltz A. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis Vol. 2 (1999), Springer, Berlin 513-538
    • (1999) Comprehensive Asymmetric Catalysis , vol.2 , pp. 513-538
    • Pfaltz, A.1
  • 71
    • 27944451724 scopus 로고    scopus 로고
    • After submission of this manuscript (on November 17), we became aware of some related work by Xu (published on November 25), who prepared bisoxazolines with a cyclohexane backbone. Applications of such compounds in asymmetric aziridinations of chalcones led to excellent enantioselectivities.
    • After submission of this manuscript (on November 17), we became aware of some related work by Xu (published on November 25), who prepared bisoxazolines with a cyclohexane backbone. Applications of such compounds in asymmetric aziridinations of chalcones led to excellent enantioselectivities. Ma L., Du D.-M., and Xu J. J. Org. Chem. 70 (2005) 10155-10158
    • (2005) J. Org. Chem. , vol.70 , pp. 10155-10158
    • Ma, L.1    Du, D.-M.2    Xu, J.3


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