Hydrogen-Bond-Mediated Enantio- and Regioselectivity in a Ru-Catalyzed Epoxidation Reaction
Hydrogen-Bond-Mediated Enantio- and Regioselectivity in a Ru-Catalyzed Epoxidation Reaction
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DOI：
10.1021/ja107601k
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发表时间：
2010-11-17
影响因子：
15
通讯作者：
Bach, Thorsten
中科院分区：
文献类型：
--
作者：
Fackler, Philipp;Berthold, Carola;Bach, Thorsten
合成了一种基于三环八氢- 1h -4,7-甲烷异吲哚-1- 1支架的手性环氧化催化剂，其中氢键位点与催化活性钌中心在空间上分离。结果表明，这种超分子催化剂的环氧化反应具有很高的对映体选择性和区域选择性，因为氢键使底物暴露于具有明显构象偏好的钌卟啉络合物中。3-乙烯基喹诺酮的环氧化反应在95% ee（71%产率）下进行。
A chiral epoxidation catalyst based on a tricyclic octahydro-1H-4,7-methanoisoindol-1-one scaffold, in which a hydrogen bonding site and the catalytically active ruthenium center are spatially separated, was synthesized. It was shown that epoxidation reactions in such a supramolecular catalyst occur with high enantio- and regioselectivity because the hydrogen bonds expose the substrate to the ruthenium porphyrin complex with a clear conformational preference. The epoxidation of 3-vinylquinolone proceeded in up to 95% ee (71% yield).