Electroreductive intramolecular coupling of aliphatic cyclic imides with ketones and O-methyloximes

被引：14
|
作者：
Kise, Naoki [1 ]
Fukazawa, Kazuaki [1 ]
Sakurai, Toshihiko [1 ]
机构：
[1] Tottori Univ, Dept Chem & Biotechnol, Grad Sch Engn, Tottori 6808552, Japan
来源：
TETRAHEDRON LETTERS | 2010年 / 51卷 / 44期
关键词：
Reductive coupling; Electroreduction; Cyclic imides; Pyrrolizidines; Indolizidines; Quinolizidines; Pyrroloazepins; TITANIUM-MEDIATED CYCLIZATION; STEREOCHEMISTRY; EPIQUINAMIDE;
D O I：
10.1016/j.tetlet.2010.08.081
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The electroreductive intramolecular coupling of aliphatic cyclic imides with ketones in isopropanol gave five- and six-membered cyclized products. S milady, the electroreductive intramolecular coupling of aliphatic cyclic imides with O-methyloximes afforded five-, six-, and seven-membered cyclized products. These reactions provide a useful method to synthesize azabicyclo[n.m.0] compounds. The bicyclic products were stereoselectively transformed to the corresponding deoxylated compounds by reduction with NaB(CN)H-3 or Et3SiH/BF3 center dot Et2O. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5767 / 5770
页数：4
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