Catalytic asymmetric Michael and Nef-type sequential reaction of nitroolefin with azlactone to construct oxazole-fused succinimide†

IF 4.3 2区 化学 Q2 CHEMISTRY, MULTIDISCIPLINARY Chemical Communications Pub Date : 2024-10-21 DOI:10.1039/d4cc04858j
Rui Weng , Yuqiao Zhou , Yaqin Zhang , Xiaoming Feng , Xiaohua Liu
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Abstract

A series of oxazole-fused succinimides bearing vicinal quaternary carbon centers were synthesized. This process takes place between nitroolefins and azlactones in the presence of a bifunctional chiral guanidine-sulfonamide organocatalyst, followed by a Nef-type transformation under the treatment of DMAP/Ac2O. Several control experiments were conducted to propose the mechanism.

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硝基烯烃与氮杂环丁内酯的催化不对称迈克尔和 Nef 型顺序反应生成草唑融合琥珀酰亚胺
我们合成了一系列带有邻接季碳中心的噁唑融合琥珀酰亚胺。该过程在双功能手性胍-磺酰胺有机催化剂存在下发生在硝基烯烃和氮内酯之间,然后在 DMAP/Ac2O 处理下发生 Nef 型转化。为了提出这一机理,进行了一些对照实验。
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来源期刊
Chemical Communications
Chemical Communications 化学-化学综合
CiteScore
8.60
自引率
4.10%
发文量
2705
审稿时长
1.4 months
期刊介绍: ChemComm (Chemical Communications) is renowned as the fastest publisher of articles providing information on new avenues of research, drawn from all the world''s major areas of chemical research.
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