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Updated: May 15, 2025

Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Published on: February 6, 2019

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2H-アジリネのカスケードエネルギー移転によるストレインリリース駆動型 [3 + 2]サイクロアディションを可能にするサイクル双機能反応剤

Alessia Petti1, Mathis J Karrasch1, Preeti Chahar1

  • 1Organisch-Chemisches Institut, Universität Münster, Corrensstraße 36, Münster 48149, Germany.

Journal of the American Chemical Society
|April 10, 2025
PubMed
まとめ

エネルギー伝達 (EnT) 誘導反応は,イソクサゾロンからストレートされた2H-アジリンを生成する. これらの中間物質はサイクル添加を経て,ピロリジン誘導体や他の有価な化合物を生成する.

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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic...
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