Asymmetric Büchner reaction and arene cyclopropanation via copper-catalyzed controllable cyclization of diynes

IF 14.7 1区 综合性期刊 Q1 MULTIDISCIPLINARY SCIENCES
Yan-Xin Zheng, Li-Gao Liu, Tian-Qi Hu, Xiao Li, Zhou Xu, Xin Hong, Xin Lu, Bo Zhou, Long-Wu Ye
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引用次数: 0

Abstract

The asymmetric Büchner reaction and related arene cyclopropanations represent one type of the powerful methods for enantioselective dearomatization. However, examples of asymmetric Büchner reactions via a non-diazo approach are quite scarce, and the related arene cyclopropanation based on alkynes has not been reported. Herein, we disclose an asymmetric Büchner reaction and the related arene cyclopropanation by copper-catalyzed controllable cyclization of N-propargyl ynamides via vinyl cation intermediates, leading to chiral tricycle-fused cycloheptatrienes and benzonorcaradienes in high yields and enantioselectivities. Importantly, this protocol represents an asymmetric arene cyclopropanation reaction of alkynes and an asymmetric Büchner reaction based on vinyl cations.

Abstract Image

铜催化二炔可控环化的不对称布赫纳反应和炔环丙烷化反应
不对称 Büchner 反应和相关的炔环丙烷化反应是一种强大的对映选择性脱芳烃方法。然而,通过非重氮方法进行不对称 Büchner 反应的实例非常少,而基于炔烃的相关炔环丙烷化反应也未见报道。在此,我们通过乙烯基阳离子中间体铜催化 N-丙炔基亚甲基酰胺的可控环化,公开了一种不对称的 Büchner 反应和相关的炔环丙烷化反应,从而以高产率和高对映选择性得到手性三环融合环庚三烯和苯并壬二烯。重要的是,该方案代表了炔烃的不对称炔环丙烷化反应和基于乙烯基阳离子的不对称布赫纳反应。
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来源期刊
Nature Communications
Nature Communications Biological Science Disciplines-
CiteScore
24.90
自引率
2.40%
发文量
6928
审稿时长
3.7 months
期刊介绍: Nature Communications, an open-access journal, publishes high-quality research spanning all areas of the natural sciences. Papers featured in the journal showcase significant advances relevant to specialists in each respective field. With a 2-year impact factor of 16.6 (2022) and a median time of 8 days from submission to the first editorial decision, Nature Communications is committed to rapid dissemination of research findings. As a multidisciplinary journal, it welcomes contributions from biological, health, physical, chemical, Earth, social, mathematical, applied, and engineering sciences, aiming to highlight important breakthroughs within each domain.
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