Title of article :
Electroreductive intramolecular coupling of aliphatic cyclic imides with α,β-unsaturated esters and ketones: unusual methyl-alkoxy exchange in silyl ketene acetals
Author/Authors :
Kise، نويسنده , , Naoki and Inoue، نويسنده , , Yusuke and Sakurai، نويسنده , , Toshihiko، نويسنده ,
Issue Information :
هفته نامه با شماره پیاپی سال 2013
Pages :
5
From page :
3281
To page :
3285
Abstract :
The electroreductive intramolecular coupling of aliphatic cyclic imides with α,β-unsaturated esters in the presence of chlorotrimethylsilane and subsequent desilylation with TBAF gave five- and six-membered cyclized esters and one-carbon elongated methyl ketones. These methyl ketones were formed by methyl-alkoxy exchange in intermediate silyl ketene acetals. The same methyl ketones were also obtained by the electroreductive intramolecular coupling of aliphatic cyclic imides with α,β-unsaturated methyl ketones. The cyclized methyl ketones were transformed to the known indolizidine and quinolizidine alkaloids, (±)-tashiromine and (±)-epilupinine.
Keywords :
Cyclic imides , indolizidines , Electroreduction , quinolizidines , reductive coupling , Pyrrolizidines
Journal title :
Tetrahedron Letters
Serial Year :
2013
Journal title :
Tetrahedron Letters
Record number :
1884733
Link To Document :
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