Unexpected Formation of Optically Active 4-Substituted 5-Hydroxy-γ-lactams by Organocatalyzed Reaction of 3-Substituted Cyclobutanones with Nitrosobenzene
Unexpected Formation of Optically Active 4-Substituted 5-Hydroxy-γ-lactams by Organocatalyzed Reaction of 3-Substituted Cyclobutanones with Nitrosobenzene
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DOI：
10.1055/s-0030-1259084
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发表时间：
2011-01-01
期刊：
影响因子：
2
通讯作者：
Secci, Francesco
中科院分区：
文献类型：
--
作者：
Capitta, Francesco;Frongia, Angelo;Secci, Francesco
本文报道了一种有机催化的3-取代环丁酮的不对称化反应，该反应可将3-取代环丁酮转化为4-取代5-羟基γ-内酰胺。这涉及扩环O-亚硝基醛醇环化多米诺序列。该合成方案提供了以良好的产率获得五元环系统的途径，并产生了两个新的立体中心。
An organocatalyzed enantioselective desymmetrization reaction for converting 3-substituted cyclobutanones into 4-substituted 5-hydroxy-gamma-lactams is presented. This involves a ring-expanding O-nitroso aldol-cyclization domino sequence. This synthetic protocol provides access to five-membered ring systems in good yields with the generation of two new stereogenic centers.