通过电化学方法生成的手性 α-氨基卡宾化合物中间体进行对映选择性 SN1 型反应

IF 14.7 1区综合性期刊 Q1 MULTIDISCIPLINARY SCIENCES

Nature Communications Pub Date : 2024-08-12 DOI:10.1038/s41467-024-50945-2

Qifeng Lin, Yingdong Duan, Yao Li, Ruijun Jian, Kai Yang, Zongbin Jia, Yu Xia, Long Zhang, Sanzhong Luo

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引用次数: 0

摘要

通过碳位中间体进行的电化学反应仍然是以可持续的方式建立分子功能性和复杂性的基本转化过程。在高离子电解质溶液中，对此类过程进行对映选择性控制是一项巨大挑战。在此，我们报告了一种通过烯胺催化阳极生成手性 α-亚氨基碳化中间体的方法。手性碳位中间体可被醇、水和硫醇等多种亲核物截取，并具有很高的立体选择性。关键的 SN1 步骤是通过叔胺介导的质子穿梭来进行的，这有助于在与卡宾化合物反应时进行面选择。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Enantioselective SN1-type reaction via electrochemically generated chiral α-Imino carbocation intermediate

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Enantioselective SN1-type reaction via electrochemically generated chiral α-Imino carbocation intermediate

Electrochemical reactions via carbocation intermediates remain fundamental transformations that build up molecular functionality and complexity in a sustainable manner. Enantioselective control of such processes is a great challenge in a highly ionic electrolyte solution. Here, we report an anodic generation of chiral α-imino carbocation intermediates by enamine catalysis. The chiral carbocation intermediates can be intercepted by a variety of nucleophiles such as alcohols, water and thiols with high stereoselectivity. The key S_N1 step proceeds via a tertiary amine-mediated proton shuttle that facilitates facial selection in reacting with carbocation.

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来源期刊

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.