二氧化矽催化吲哚烯丙基化之Friedel-Crafts反應
Abstract
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.
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.
Description
Keywords
吲哚, indole