Electroreductive Intermolecular Coupling of 3-Methoxycarbonylindoles with Ketones

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• 作者：Naoki Kise ; Akinori Sueyoshi ; Shin-ichirou Takeuchi ; Toshihiko Sakurai
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：June 7, 2013
• 年：2013
• 卷：15
• 期：11
• 页码：2746-2749
• 全文大小：271K
• 年卷期：v.15,no.11(June 7, 2013)
• ISSN：1523-7052

文摘

The electroreductive coupling of 1-alkoxycarbonyl-3-methoxycarbonylindoles with aromatic ketones in the presence of chlorotrimethylsilane gave cis-adducts stereoselectively. The cis-adducts were readily transformed to trans-adducts by treatment with catalyst DBU. On the other hand, the electroreductive coupling of 1-methyl-3-methoxycarbonylindole with aliphatic ketones in isopropanol afforded trans-adducts exclusively. The adducts are the precursors for the synthesis of 2-substituted 3-methoxycarbonylindoles and indolines.