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5-芳基戊-2,4-二烯酸的模板导向选择性光二聚反应

Template-Directed Selective Photodimerization Reactions of 5-Arylpenta-2,4-dienoic Acids.

作者信息

Munir Badar, Yagci Bilge Banu, Zorlu Yunus, Türkmen Yunus E

机构信息

Department of Chemistry, Faculty of Science, Bilkent University, Ankara 06800, Türkiye.

Department of Chemistry, Gebze Technical University, Gebze, Kocaeli 41400, Türkiye.

出版信息

J Org Chem. 2024 Jul 19;89(14):10409-10418. doi: 10.1021/acs.joc.4c01374. Epub 2024 Jul 10.

DOI:10.1021/acs.joc.4c01374
PMID:38984741
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11267613/
Abstract

We developed an efficient method that enables selective photodimerization of 5-arylpenta-2,4-dienoic acids (i.e., vinylogous cinnamic acids). The use of 1,8-dihydroxynaphthalene as a template ensures proximity of the two reacting olefins so that irradiation of template-bound dienoic acids gives mono [2 + 2] cycloaddition products in good to excellent yields (up to 99%), as single regioisomers, and with high diastereoselectivities (dr = 3:1 to 13:1). The geometrical and stereochemical features of compounds , , and were analyzed by X-ray crystallography.

摘要

我们开发了一种高效方法，该方法能够实现5-芳基戊-2,4-二烯酸（即乙烯基肉桂酸）的选择性光二聚反应。使用1,8-二羟基萘作为模板可确保两个反应烯烃相互靠近，因此对与模板结合的二烯酸进行辐照可得到产率良好至优异（高达99%）的单[2 + 2]环加成产物，为单一区域异构体，且具有高非对映选择性（dr = 3:1至13:1）。通过X射线晶体学分析了化合物、和的几何和立体化学特征。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/078c/11267613/4a7063bddd4b/jo4c01374_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/078c/11267613/fa691a2da485/jo4c01374_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/078c/11267613/9f0943c4dad2/jo4c01374_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/078c/11267613/89ec3473dff3/jo4c01374_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/078c/11267613/b642dd1a3d00/jo4c01374_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/078c/11267613/477f2fb48ae8/jo4c01374_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/078c/11267613/4a7063bddd4b/jo4c01374_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/078c/11267613/fa691a2da485/jo4c01374_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/078c/11267613/9f0943c4dad2/jo4c01374_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/078c/11267613/89ec3473dff3/jo4c01374_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/078c/11267613/b642dd1a3d00/jo4c01374_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/078c/11267613/477f2fb48ae8/jo4c01374_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/078c/11267613/4a7063bddd4b/jo4c01374_0006.jpg

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