Ni-Catalyzed Enantioselective C-Acylation of α-Substituted Lactams.
Ni-Catalyzed Enantioselective C-Acylation of α-Substituted Lactams.
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DOI：
10.1021/jacs.6b02120
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发表时间：
2016-07-27
影响因子：
15
通讯作者：
Stoltz BM
中科院分区：
文献类型：
--
作者：
Hayashi M;Bachman S;Hashimoto S;Eichman CC;Stoltz BM
报道了一种催化不对称选择性C-酰化反应合成α-季铵取代内酰胺的新方法。镍催化的内酰胺烯醇化物、苯甲腈和芳基卤化物的三组分偶联产生β-亚氨基内酰胺，然后通过酸水解得到β-酮基内酰胺。使用容易获得的Mandyphos型配体和添加LiBr使得能够在α-取代的内酰胺上构建季立体中心以形成高达94%ee的β-酮基内酰胺。
A new strategy for the catalytic enantioselective C-acylation to generate α-quaternary substituted lactams is reported. Ni-catalyzed three-component coupling of lactam enolates, benzonitriles, and aryl halides produce β-imino lactams that then afford β-keto lactams by acid hydrolysis. Use of a readily available Mandyphos- ype ligand and the addition of LiBr enables the construction of quaternary stereocenters on α-substituted lactams to form β-keto lactams in up to 94% ee.