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能量转移引发的[2π + 2σ]环加成反应在双环[2.1.1]己烷合成中的应用。

Strain-Release [2π + 2σ] Cycloadditions for the Synthesis of Bicyclo[2.1.1]hexanes Initiated by Energy Transfer.

机构信息

Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405, United States.

SpiroChem AG, Rosental area, WRO-1047-3, Mattenstrasse 22, 4058 Basel, Switzerland.

出版信息

J Am Chem Soc. 2022 May 11;144(18):7988-7994. doi: 10.1021/jacs.2c02976. Epub 2022 Apr 27.

DOI:10.1021/jacs.2c02976
PMID:35476547
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9832330/
Abstract

Saturated bicycles are becoming ever more important in the design and development of new pharmaceuticals. Here a new strategy for the synthesis of bicyclo[2.1.1]hexanes is described. These bicycles are significant because they have defined exit vectors, yet many substitution patterns are underexplored as building blocks. The process involves sensitization of a bicyclo[1.1.0]butane followed by cycloaddition with an alkene. The scope and mechanistic details of the method are discussed.

摘要

饱和自行车在新药物的设计和开发中变得越来越重要。这里描述了一种合成双环[2.1.1]己烷的新策略。这些自行车很重要，因为它们具有确定的出口向量，但许多取代模式作为构建块还未得到充分探索。该过程涉及双环[1.1.0]丁烷的敏化，然后与烯烃进行环加成。讨论了该方法的范围和机理细节。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/be51/9832330/9003965cb21b/nihms-1862498-f0009.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/be51/9832330/cbefa9337977/nihms-1862498-f0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/be51/9832330/f379187be3a4/nihms-1862498-f0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/be51/9832330/afe514ffe573/nihms-1862498-f0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/be51/9832330/9003965cb21b/nihms-1862498-f0009.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/be51/9832330/9003965cb21b/nihms-1862498-f0009.jpg

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