本論文旨在探討以二氧化矽及有機催化劑催化Friedel-Crafts反應合成吲哚之烯丙基化產物。近年來發現許多天然物分子含有吲哚之分子結構，因具有生物活性，可應用於藥物分子的合成。我們以二氧化矽催化引朵與allylic acetate 40進行Friedel-Crafts反應，得到高產率的引朵烯丙基化產物，且大量製備仍然可以保持77%的產率；也嘗試使用有機催化劑催化其反應，眾多篩選反應後，發現以20 mol%的催化劑55，在二氯甲烷為溶劑下，可得到最佳產率9%及鏡像超越值20% ee，結果並不理想。後續研究在進行中，期望能夠找到合適的催化劑或者修飾起始物的官能基，使既有之催化劑能夠與起始物有更好的反應，改善產率及鏡像超越值。

This dissertation focus on the use of silica-gel and organocatalyst to catalyze the Friedel-Crafts reaction of indole with allylic acetate 40. In recent years, indole derivatives has been found in many natural products, and their already used in a lot of pharmaceuticals because of their biological activities. In our lab we found that useing silica-gel as medium can get a high yield of indole allylation product, even if in large scale we can get 77% yield. We also use amounts of organocatalysts try to get some enantioselectivities, but the best result we can get only 9% yield and 20% ee when use 20mol % organocatalyst 55. In the future, we will continue this article, to get a high yield and high enantioselectivity is our objective, we will try to modify the substrate make it easier to interact with the catalyst, or to find some new catalysts.

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