利用一價銠金屬經由動力學拆分催化有機硼酸及外消旋環戊烯酮:合成前列腺素及其衍生物
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2018
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Abstract
本篇論文主要為探討使用一價銠金屬與掌性雙環[2.2.2]配基L2催化芳香性及烯基硼酸試劑68對外消旋起始物(±)-70進行1,4-共軛加成反應(conjugate addition),經由動力學拆分(kinetic resolution),得到化合物109,鏡像選擇性最高達到>99.5%,產率接近50%。將其再利用two-component的方式去合成出目標天然物前列腺素及其衍生物:PGE1 (31; 24% yield), PGA1 methyl ester (65; 9% yield), PGF1α (113; 24% yield)。
This thesis describes the enantioselective conjugate addition reaction of racemic starting material 70 with boronic acid 68 by using Rh(Ⅰ)/L2g catalyst via a with kinetic resolution manner. Compound 109 was obtained with ee up to >99.5% and the yield approximately 50%. This two-component method witnesses its synthetic applications in the synthesis of prostaglandin derivatives: PGE1 (31; 24% yield), PGA1 methyl ester (65; 9% yield), PGF1α (113; 24% yield).
This thesis describes the enantioselective conjugate addition reaction of racemic starting material 70 with boronic acid 68 by using Rh(Ⅰ)/L2g catalyst via a with kinetic resolution manner. Compound 109 was obtained with ee up to >99.5% and the yield approximately 50%. This two-component method witnesses its synthetic applications in the synthesis of prostaglandin derivatives: PGE1 (31; 24% yield), PGA1 methyl ester (65; 9% yield), PGF1α (113; 24% yield).
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一價銠金屬, 動力學拆分, 外消旋環戊烯酮, 前列腺素, Rh(I), Kinetic Resolution, (±)-4-Siloxy Cyclopentenones, Prostaglandins