Plietker Bernd, Niggemann Meike
Organische Chemie II, Fachbereich Chemie, Universitat Dortmund, Otto-Hahn-Str. 6, D-44221, Dortmund, Germany.
Org Biomol Chem. 2004 Sep 7;2(17):2403-7. doi: 10.1039/B407937J. Epub 2004 Aug 5.
Alpha-hydroxy ketones are versatile intermediates for the synthesis of complex molecular architectures and subunits of a variety of natural products. Different approaches towards the synthesis of this important functional group combination have been elaborated. The present article summarises our research on the field of RuO4-catalysed oxidations of alkenes that resulted in the development of the first RuO4-catalysed ketohydroxylation of olefins. Mechanistic investigations of both dihydroxylation and ketohydroxylation led to the discovery of the first regioselective catalytic mono oxidation of vic-diols, which was applied in a two-step sequence of asymmetric dihydroxylation and regioselective mono oxidation to furnish enantiopure alpha-hydroxy ketones with both predictable regioselectivity and absolute configuration.
α-羟基酮是用于合成复杂分子结构和多种天然产物亚基的通用中间体。人们已经阐述了合成这种重要官能团组合的不同方法。本文总结了我们在RuO₄催化烯烃氧化领域的研究，该研究导致了首例RuO₄催化的烯烃酮羟基化反应的开发。对二羟基化和酮羟基化的机理研究导致发现了首例区域选择性催化邻二醇单氧化反应，该反应应用于不对称二羟基化和区域选择性单氧化的两步序列中，以提供具有可预测区域选择性和绝对构型的对映体纯α-羟基酮。
