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  • 學位論文

以不對稱有機催化在水相中利用吲哚酮亞甲基假吲哚進行硫化加成反應合成具掌性之3,3-雙取代吲哚酮化合物

Organocatalytic Enantioselective Thiolation with Oxindolylideneindolenines on Water: Synthesis of 3,3-Disubstituted Oxindoles

指導教授 : 韓政良

摘要


本論文旨在開發在水相中以吲哚酮亞甲基假吲哚化合物 (Oxindolylideneindolenines) 和硫醇化合物(Thiol) 以雙功能金雞納生物鹼-硫脲之有機催化劑 (cinchona alkaloid-thiourea bifunctional organo-catalyst) 進行不對稱有機催化硫化加成反應 (organocatalystic enantioselective thiolation) 建立出具選擇性四級立體中心之3,3-雙取代吲哚酮化合物,在通用性測試上有鏡像選擇性 (36-97%) 與產率 (17-56%) 的結果。 此外此系列化合物具有3,3-雙取代吲哚酮骨架,未來可進行生物活性的探討。

並列摘要


The primary concern of this study is to explore the research on the development of an organocatalytic enantioselective thiolation of oxindolylideneindolenines and thiols compound on water. This reaction was catalyzed by a cinchona alkaloid-thiourea bifunction organocatalyst, producing products in normal enantioselectivites (36-97%) and yield (17-56%). Besides this, this series compound contain 3,3-disubstituted oxindole skeleton, we may do some biological activity test in the future.

參考文獻


2.Eriksson, T.; Björkman, S.; Höglund, P. Eur. J. Clin. PHarmacol. 2001, 57, 365-376.
3.Nakamura, K.; Yamanaka, R.; Matsuda, T.; Harada, T. Tetrahedron Asymmetry. 2003, 14, 2659-2681.
6.Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615-1621.
9.Berkessel, A.; Gröger, H. Asymmetric organocatalysis - From Biomimetic Concepts to Application in Asymmetric Synthesis, 1st ed.; Wiley-VCH: Germany, 2005.
11.Yeboah, E. M.; Yeboah, S. O.; Singh, G. S. Tetrahedron. 2011, 67, 1725-1762.

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