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首页> 外文期刊>Chemistry: A European journal >Chiral BrOnsted Acid Directed Iron-Catalyzed Enantioselective Friedel– Crafts Alkylation of Indoles with b-Aryl a -Hydroxy Enones
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Chiral BrOnsted Acid Directed Iron-Catalyzed Enantioselective Friedel– Crafts Alkylation of Indoles with b-Aryl a -Hydroxy Enones

机译：手性布朗斯台德酸定向铁催化的对映选择性弗瑞德-用b-芳基α-羟基烯酮使吲哚烷基化

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摘要

A cooperative catalytic system established by the combination of an iron salt and a chiral Bronsted acid has proven to be effective in the asymmetric Friedel–Crafts alkylation of indoles with b-aryl a -hydroxy enones. Good to excellent yields and enatioselectivities were observed for a variety of a -hydroxy enones and indoles, particularly for the b-aryl a -hydroxy enones bearing an electron-withdrawing group at the para position of the phenyl ring (up to 90% yield and 91% ee). The proton of the chiral Bronsted acid, the Lewis acid activation site, as well as the inherent basic site for the hydrogen-bonding interaction of the Bronsted acid are responsible for the high catalytic activities and enantioselectivities of the title reaction. A possible reaction mechanism was proposed. The key catalytic species in the catalytic system, the phosphate salt of FeIII, which was thought to be responsible for the high activity and good enantioselectivity, was then confirmed by ESIMS studies.
机译：铁盐和手性布朗斯台德酸的组合建立的协同催化体系已被证明可有效地将吲哚与b-芳基α-羟基烯酮进行不对称的Friedel-Crafts烷基化反应。对于各种α-羟基烯酮和吲哚，特别是对于在苯环对位带有吸电子基团的b-芳基α-羟基烯酮，观察到良好的至优异的产率和对映选择性（高达90％的产率和91％ee）。手性布朗斯台德酸的质子，路易斯酸的活化位点以及布朗斯台德酸的氢键相互作用的固有碱性位点负责标题反应的高催化活性和对映选择性。提出了一种可能的反应机理。然后通过ESIMS研究确认了催化体系中的关键催化物质FeIII的磷酸盐，该盐被认为具有高活性和良好的对映选择性。

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