The Catalytic Asymmetric Fischer Indolization

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• 作者：Steffen M眉ller ; Matthew J. Webber ; Benjamin List
• 刊名：Journal of the American Chemical Society
• 出版年：2011
• 出版时间：November 23, 2011
• 年：2011
• 卷：133
• 期：46
• 页码：18534-18537
• 全文大小：833K
• 年卷期：v.133,no.46(November 23, 2011)
• ISSN：1520-5126

文摘

The first catalytic asymmetric Fischer indolization is reported. In the presence of a 5 mol % loading of a novel spirocyclic chiral phosphoric acid, 4-substituted cyclohexanone-derived phenylhydrazones undergo a highly enantioselective indolization. Efficient catalyst turnover was achieved by the addition of a weakly acidic cation exchange resin, which removes the generated ammonia. The reaction can be conducted under mild conditions and gives various 3-substituted tetrahydrocarbazoles in generally high yields.