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Highly Enantioselective Construction of Polycyclic Spirooxindoles by Organocatalytic 1,3-Dipolar Cycloaddition of 2-Cyclohexenone Catalyzed by Proline-Sulfonamide

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Abstract
  • An enantioselective 1,3-dipolar cycloaddition of 2-cyclo-hexene-1-one and azomethine ylide generated in situ from isatin and amino ester was developed by employing proline sulfonamide as the catalyst. Consequently, novel polycyclic spirooxindole scaffolds with three contiguous stereocenters were prepared in high yield (up to 95%) with excellent diastereo- (> 20:1 dr) and enantio-selectivity (up to 99% ee).
  • Keywords: Isatin, Spiro compounds, Organocatalysis, Cycloaddition, Nitrogen heterocycles, Spirooxindole, 2-cyclohexene-1-one, Alkaloids, 1,3-dipolar cycloaddition
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Citation
  • Xiao, J. A., Liu, Q., Ren, J. W., Liu, J., Carter, R. G., Chen, X. Q., & Yang, H. (2014). Highly Enantioselective Construction of Polycyclic Spirooxindoles by Organocatalytic 1,3‐Dipolar Cycloaddition of 2‐Cyclohexenone Catalyzed by Proline‐Sulfonamide. European Journal of Organic Chemistry, 2014(26), 5700-5704. doi: 10.1002/ejoc.201402953
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  • 2014
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  • 26
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  • We gratefully acknowledge the financial support from National Natural Science Foundation of China (21175155, 21276282 & 21376270), Hunan Provincial Science & Technology Department (2012WK2007), and Central South University.
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