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33645887379
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note
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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.
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34
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0014435890
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33645851493
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note
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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.
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Evans D.A., Murry J.A., von Matt P., Norcross R.D., and Miller S.J. Angew. Chem. 107 (1995) 864-867
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For a general overview on the Lewis acid catalyzed Diels-Alder reaction see:. Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds), Springer, Berlin
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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
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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
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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
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Ooi, T.1
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Reviews:. Beller M., and Bolm C. (Eds), Wiley-VCH, Weinheim
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Reviews:. Gladiari S., and Alberico E. In: Beller M., and Bolm C. (Eds). Transition Metals for Organic Synthesis. 2nd ed. Vol. 2 (2004), Wiley-VCH, Weinheim 145-166
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Reviews:. Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds), Springer, Berlin
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Reviews:. Pfaltz A. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis Vol. 2 (1999), Springer, Berlin 513-538
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Hetero-Diels-Alder reaction:. Bolm C., Verrucci M., Simic O., Cozzi P.G., Raabe G., and Okamura H. Chem. Commun. (2003) 2826-2827
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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.
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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
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