Electroreductive coupling of aromatic ketones, aldehydes, and aldimines with α,β-unsaturated esters: Synthesis of 5-aryl substituted γ-butyrolactones and lactams

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• 作者：Naoki Kise ; ^{kise@bio.tottori-u.ac.jp} ; Yusuke Hamada ; Toshihiko Sakurai
• 关键词：Reductive coupling ; Electroreduction ; Aromatic ketones ; Aromatic aldimines ; γ-Butyrolactones ; γ-Butyrolactams
• 刊名：Tetrahedron
• 出版年：2017
• 出版时间：23 February 2017
• 年：2017
• 卷：73
• 期：8
• 页码：1143-1156
• 全文大小：792 K
• 卷排序：73

文摘

The electroreductive intermolecular coupling of aromatic ketones and aldehydes with α,β-unsaturated esters in the presence of TMSCl gave the adducts as γ-trimethylsiloxy esters. The detrimethylsilylation of the adducts with TBAF afforded 5-aryl substituted γ-butyrolactones. The electroreductive coupling of N-(4-methoxyphenyl)-1-arylmethaneimines with methyl acrylate in the presence of TMSCl gave the adducts as methyl 4-aryl-4-((4-methoxyphenyl)amino)butanoates. The adducts were transformed to 5-aryl-γ-butyrolactams by cyclization with NaH and subsequent oxidation with CAN. (±)-Norcotinine was prepared from nicotinaldehyde by this method. The electroreductive coupling of aromatic ketones and aldimines with acrylonitrile in the presence of TMSCl gave 4-aryl-4-(trimethylsiloxy)butanenitriles and 4-aryl-4-((4-methoxyphenyl)amino)butanenitriles, respectively.