A mild procedure for the Lewis acid-catalyzed ring-opening of activated cyclopropanes with amine nucleophiles
A mild procedure for the Lewis acid-catalyzed ring-opening of activated cyclopropanes with amine nucleophiles
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DOI：
10.1021/ol8009286
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发表时间：
2008-07-03
期刊：
影响因子：
5.2
通讯作者：
Charette, Andre B.
中科院分区：
文献类型：
--
作者：
Lifchits, Olga;Charette, Andre B.
描述了路易斯酸催化 1-硝基环丙烷甲酸甲酯与胺亲核试剂的开环反应。该反应在室温下进行，并且从环丙烷的亲电子中心到无环产物的对映体纯度完全保持。该方法应用于双血清素/去甲肾上腺素再摄取抑制剂 (3R)-3-(1H-吲哚-1-基)-N-甲基-3-苯基丙-1-胺的对映选择性合成。
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.