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

被引：8
|
作者：
Kise, Naoki [1 ]
Hamada, Yusuke [1 ]
Sakurai, Toshihiko [1 ]
机构：
[1] Tottori Univ, Grad Sch Engn, Dept Chem & Biotechnol, 4-101 Koyama Cho Minami, Tottori 6808552, Japan
来源：
TETRAHEDRON | 2017年 / 73卷 / 08期
关键词：
Reductive coupling; Electroreduction; Aromatic ketones; Aromatic aldimines; gamma-Butyrolactones; gamma-Butyrolactams; ASYMMETRIC TRANSFER HYDROGENATION; ELECTROORGANIC CHEMISTRY; CYCLOPROPANES; ALKENES;
D O I：
10.1016/j.tet.2017.01.013
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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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页码：1143 / 1156
页数：14
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