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通过由生成的CF-醌甲基化物和硫叶立德进行[4+1]环化反应实现CF-二氢苯并呋喃的非对映选择性合成。

Diastereoselective synthesis of CF-dihydrobenzofurans by [4+1] annulation of -generated CF--quinone methides and sulfur ylides.

作者信息

Jha Babli K, Prudhviraj Jaggaraju, Mainkar Prathama S, Punna Nagender, Chandrasekhar Srivari

机构信息

Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology Hyderabad 500007 India

Academy of Scientific and Innovative Research (AcSIR) Ghaziabad 201002 India.

出版信息

RSC Adv. 2020 Oct 20;10(63):38588-38591. doi: 10.1039/d0ra08289a. eCollection 2020 Oct 15.

DOI:10.1039/d0ra08289a
PMID:35517513
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9057278/
Abstract

An efficient and highly diastereoselective synthesis of CF-dihydrobenzofurans by the reaction of -generated CF-QMs in the presence of a base with sulphur ylides is put forward. The generality of the present developed method was well studied with diverse substrates to access the corresponding products in excellent yields. The highly reactive CF-QM has been utilized first time for the annulation reaction.

摘要

提出了一种在碱存在下，通过生成的CF-QMs与硫叶立德反应高效且高非对映选择性地合成CF-二氢苯并呋喃的方法。用多种底物对本开发方法的通用性进行了深入研究，以优异的产率获得相应产物。高反应活性的CF-QM首次用于环化反应。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d90/9057278/4c89c98afb3a/d0ra08289a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d90/9057278/7ea9eb30b406/d0ra08289a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d90/9057278/2b5374a159e7/d0ra08289a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d90/9057278/4c89c98afb3a/d0ra08289a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d90/9057278/7ea9eb30b406/d0ra08289a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d90/9057278/2b5374a159e7/d0ra08289a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d90/9057278/4c89c98afb3a/d0ra08289a-f2.jpg

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本文引用的文献

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通过对醌甲叉及其衍生物的合成α-CF-α-季酮，并将其衍生为具有连续拥挤的立体中心的化合物。
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Catalyst-Free Synthesis of 2,3-Dihydrobenzofurans via a Formal [4+1] Annulation of Propargylamines with Sulfur Ylides.通过炔丙胺与硫叶立德的形式上的[4+1]环化反应无催化剂合成2,3-二氢苯并呋喃
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Recent advances in the application of Diels-Alder reactions involving o-quinodimethanes, aza-o-quinone methides and o-quinone methides in natural product total synthesis.Diels-Alder 反应在天然产物全合成中涉及邻醌二甲烷、氮杂邻醌二甲烷和邻醌二甲烷的应用的最新进展。
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