雙功能金雞納鹼催化3-高醯基香豆素與亞甲基羥吲哚進行不對稱麥可-麥可反應建構螺環羥吲哚
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Date
2019
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Abstract
螺環羥吲哚（spiroxindole）是一種特殊的骨架，出現於天然物及藥物中都很普遍，且報導指出其具有生物活性，使得化學家相繼進行深入研究。本實驗證明利用金雞鈉鹼（Cinchona alkaloid）衍生物催化羥吲哚（oxindole）衍生物，與3-高醯基香豆素（3-homoacyl coumarin）衍生物進行分子間及分子內的Michael reaction，以建構螺環羥吲哚，獲得五個相鄰的立體中心具良好產率及鏡像選擇性；同時設計起始物羥吲哚衍生物，取代基苯基（phenyl）及苯甲醯基（benzoyl group），推測在羰基（carbonyl）存在下，利用氫鍵的控制，增加選擇性，使得在優化條件下，成功得到更佳優良的鏡像選擇性。
The spirooxindole structure is a privileged scaffold that is prevalent in both natural products and synthetic bioactive molecules. Herein, we demonstrate a Cinchona alkaloid derivative catalyzed Michael/Michael cascade reaction of 3-homoacyl coumarins and arylidene or benzoylated oxindoles to construct spirooxindole derivatives. This reaction afforded the corresponding products with five contiguous stereocenters including a quaternary center in good to excellent yields with moderate to excellent enantioselectivities. The comparision between the substitutent on oxindole ring phenyl and benzoyl group, the benzoyl group has carbonyl group it shows the different results and catalyst because of the hydrogen bonding.
The spirooxindole structure is a privileged scaffold that is prevalent in both natural products and synthetic bioactive molecules. Herein, we demonstrate a Cinchona alkaloid derivative catalyzed Michael/Michael cascade reaction of 3-homoacyl coumarins and arylidene or benzoylated oxindoles to construct spirooxindole derivatives. This reaction afforded the corresponding products with five contiguous stereocenters including a quaternary center in good to excellent yields with moderate to excellent enantioselectivities. The comparision between the substitutent on oxindole ring phenyl and benzoyl group, the benzoyl group has carbonyl group it shows the different results and catalyst because of the hydrogen bonding.
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連鎖反應, 麥可/麥可反應, 螺環羥吲哚, cascade reaction, Michael/Michael reaction, spirooxindole