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电荷重排实现了顺式取代四氢呋喃的模块化和非对映选择性合成。

Charge Relocation Enables a Modular and Diastereoselective Synthesis of cis-Substituted Tetrahydrofurans.

作者信息

Niu Zhi-Jie, Brutiu Bogdan R, Riomet Margaux, Kaiser Daniel, Maulide Nuno

机构信息

Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, Vienna, 1090, Austria.

出版信息

Angew Chem Int Ed Engl. 2025 Jul;64(29):e202503750. doi: 10.1002/anie.202503750. Epub 2025 Jun 4.

DOI:10.1002/anie.202503750
PMID:40318105
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12258665/
Abstract

Diastereoselective construction of organic scaffolds from simple and commercial materials is a powerful strategy in contemporary organic synthesis. Herein, we report a novel disconnection for the direct preparation of tetrahydrofurans (THFs) and corresponding derivatives from acyl chlorides and alkenes using charge relocation. Newly synthesised Hantzsch ester derivatives, functioning both as hydride sources and selectivity modulators, enabled exceptional diastereoselectivity. The wide range of alkenes tolerated is a highlight of the method, enabling the construction of structurally distinct THF-containing skeletons.

摘要

从简单的商业原料非对映选择性构建有机骨架是当代有机合成中的一种强大策略。在此，我们报道了一种新颖的切断方法，用于通过电荷重排从酰氯和烯烃直接制备四氢呋喃（THF）及其相应衍生物。新合成的汉斯酯衍生物既作为氢化物源又作为选择性调节剂，实现了优异的非对映选择性。该方法的一大亮点是能耐受多种烯烃，可构建结构各异的含THF骨架。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c4d3/12258665/a3e2cc943560/ANIE-64-e202503750-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c4d3/12258665/89ce7ab7996b/ANIE-64-e202503750-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c4d3/12258665/921f96dddc5b/ANIE-64-e202503750-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c4d3/12258665/53751e46b164/ANIE-64-e202503750-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c4d3/12258665/a3e2cc943560/ANIE-64-e202503750-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c4d3/12258665/89ce7ab7996b/ANIE-64-e202503750-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c4d3/12258665/921f96dddc5b/ANIE-64-e202503750-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c4d3/12258665/53751e46b164/ANIE-64-e202503750-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c4d3/12258665/a3e2cc943560/ANIE-64-e202503750-g001.jpg

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本文引用的文献

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