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过渡金属催化的张力双环烯烃的多米诺反应。

Transition-metal-catalyzed domino reactions of strained bicyclic alkenes.

作者信息

Pounder Austin, Neufeld Eric, Myler Peter, Tam William

机构信息

Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph, Guelph, Ontario, N1G 2W1, Canada.

出版信息

Beilstein J Org Chem. 2023 Apr 24;19:487-540. doi: 10.3762/bjoc.19.38. eCollection 2023.

DOI:10.3762/bjoc.19.38
PMID:37153643
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10155623/
Abstract

This review presents a comprehensive overview of transition-metal-catalyzed domino reactions of strained bicyclic alkenes, including both homo- and heterobicyclic alkenes. These compounds are important synthons in organic synthesis, providing an important platform for the construction of biologically/medicinally significant compounds which bear multiple stereocenters. The review has been divided according to the metal used in the reaction. An overview of the substrate scope, reaction conditions, and their potential applications in organic synthesis is discussed. A comprehensive outlook on the reactivity paradigms of homo- and heterobicyclic alkenes is discussed and should shed light on future directions for further development in this field.

摘要

本综述全面概述了应变双环烯烃的过渡金属催化多米诺反应,包括同环和杂环双环烯烃。这些化合物是有机合成中的重要合成子,为构建具有多个立体中心的生物/医学上重要的化合物提供了重要平台。该综述根据反应中使用的金属进行了划分。讨论了底物范围、反应条件及其在有机合成中的潜在应用。还讨论了同环和杂环双环烯烃反应范式的全面展望,这应该为该领域的进一步发展指明未来方向。

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2
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Org Lett. 2022 Jul 29;24(29):5260-5265. doi: 10.1021/acs.orglett.2c01734. Epub 2022 Jul 15.
3
Nickel-Catalyzed Addition of C-C Bonds of Amides to Strained Alkenes: The 1,2-Carboaminocarbonylation Reaction.
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4
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RSC Adv. 2023 Dec 6;13(50):35617-35620. doi: 10.1039/d3ra07653a. eCollection 2023 Nov 30.
镍催化酰胺 C-C 键与张力烯烃的加成反应:1,2-碳氨羰化反应。
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4
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9
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