有機連鎖反應：鹼催化多環香豆素衍生物的非鏡像選擇性合成
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2021
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近年來，香豆素及其衍生物表現出多樣生物學活性，最常作為抗凝血劑使用，故西豆素衍生物的製備與應用成為許多人研究合成的目標。本文利用3-高醯基香豆素與2-硝基苯並呋喃進行反應，透過碳酸銫活化下，經由Michael/Michael去芳香化連鎖反應，建立多環多取代香豆素衍生物，此產物具有四個連續得立體中心，產率(52-72%)、非鏡像選擇性比例(11:1~>20:1)。不對稱合成具有高光學純度產物仍須後續探討。
In recent year, coumarin and its heterocyclic derivatives exhibit diverse biological activities, It is most commonly used as an anticoagulant,therefore, the preparation and application of coumarin derivatives has become the goal of many group’s research and synthesis. In this study, 3-homocoumarin and 2-nitrobenzofuran are used to be starting material, activated by cesium carbonate, and through a Michael/Michael dearomatization reaction to establish a polycyclic polysubstituted coumarin derivative bearing continuous four stereogenic center in moderate yield. (52-72%) , diastereoselectivities reaches (11:1~>20:1).Asymmetric synthesis of products with high enantioselectivity are still in study.
In recent year, coumarin and its heterocyclic derivatives exhibit diverse biological activities, It is most commonly used as an anticoagulant,therefore, the preparation and application of coumarin derivatives has become the goal of many group’s research and synthesis. In this study, 3-homocoumarin and 2-nitrobenzofuran are used to be starting material, activated by cesium carbonate, and through a Michael/Michael dearomatization reaction to establish a polycyclic polysubstituted coumarin derivative bearing continuous four stereogenic center in moderate yield. (52-72%) , diastereoselectivities reaches (11:1~>20:1).Asymmetric synthesis of products with high enantioselectivity are still in study.
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有機連鎖反應, 麥可加成, 去芳香化反應, 香豆素, 2-硝基苯並呋喃, coumarin, Michael addition, dearomatization