一價銠金屬催化有機硼酸與掌性環戊烯酮進行共軛加成反應合成前列腺素衍生物

Rh(I)-Catalyzed Conjugate Addition Reaction of Organoboronic Acids with a Chiral Cyclopentenone for the Synthesis of Prostaglandin Derivatives

王韻婷(Wang Yun-Ting)

指導教授 ： 吳學亮

國立臺灣師範大學/理學院/化學系/碩士(2016年)

https://doi.org/10.6345/NTNU202204537

摘要

['本篇論文在探討 (1)利用一價銠金屬作為催化劑，以甲醇當溶劑，氫氧化鉀作為鹼性添加劑，在低溫條件下(3 °C)，催化(R)-47與各種不同芳香基以及烯基硼酸的共軛加成反應，得到單一非鏡像異構物 52。此反應利用於他氟前列素 (tafluprost 3) 的合成。 (2)使用起始物(±)-68利用掌性雙環[2.2.1]配基L1與一價銠金屬形成之催化劑催化與烯基硼酸進行1,4-共軛加成反應，可以得到29−44％的產率以及90−98％的鏡像超越值。
']

關鍵字

銠金屬 ； 共軛加成 ； 前列腺素

並列摘要

['In this thesis, a conjugate reaction of a variety of aryl- and alkenyl- boronic acids, in the presence of 1.5 mol% of [RhCl(COD)]2 catalyst with (R)-47 is described. The conjugate addition reactions conducted at 3 °C, employing 1.2 equiv KOH as the basic additive and using MeOH as the solvent proceeded in a high diastereoselective fashion to give the conjugate adduct in 52−99% yield. In addition, the enantioselective conjugate addition reaction of 68 with 51a, catalyzed by 3 mol% of Rh(I)/L1 was also studied. Compound 79 was obtained as a single diastereomer in 90−98% ee.
']

並列關鍵字

Rh(I)-Catalyzed ； Conjugate Addition ； Prostaglandin

參考文獻

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