A mild procedure for the Lewis acid-catalyzed ring-opening of activated cyclopropanes with amine nucleophiles

被引：154
|
作者：
Lifchits, Olga [1 ]
Charette, Andre B. [1 ]
机构：
[1] Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada
来源：
ORGANIC LETTERS | 2008年 / 10卷 / 13期
关键词：
D O I：
10.1021/ol8009286
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Lewis acid-catalyzed ring-opening of methyl 1-nitrocyclopropanecarboxylates with amine nucleophiles is described. The reaction proceeds at room temperature and with complete preservation of the enantiomeric purity from the electrophilic center of the cyclopropane to the acyclic product. The methodology was applied in an enantioselective synthesis of the dual serotonin/norepinephrine reuptake inhibitor (3R)-3-(1H-indol-1-yl)-N-methyl-3-phenylpropan-1-amine.
引用
收藏
页码：2809 / 2812
页数：4
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