Journal
TETRAHEDRON
Volume 73, Issue 8, Pages 1143-1156Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2017.01.013
Keywords
Reductive coupling; Electroreduction; Aromatic ketones; Aromatic aldimines; gamma-Butyrolactones; gamma-Butyrolactams
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The electroreductive intermolecular coupling of aromatic ketones and aldehydes with alpha,beta-unsaturated esters in the presence of TMSCl gave the adducts as gamma-trimethylsiloxy esters. The detrimethylsilylation of the adducts with TBAF afforded 5-aryl substituted gamma-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-gamma-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. (C) 2017 Elsevier Ltd. All rights reserved.
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