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Cover Feature: The Baldwin Rearrangement: Synthesis of 2‐Acylaziridines (Eur. J. Org. Chem. 43/2017)
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2017-11-10 , DOI: 10.1002/ejoc.201701548
Salia Tangara 1 , Alice Kanazawa 1 , Sandrine Py 1
Affiliation  

The Cover Feature shows the synthesis of 2‐acylaziridines by Baldwin rearrangement. Known for about fifty years, the Baldwin rearrangement has remained undervalued for its potential in organic synthesis. This is quite surprising as the key substrates, 4‐isoxazolines, are readily available compounds. The cover feature illustrates the thermodynamically favoured ring‐contraction process converting highly reactive 4‐isoxazolines into more stable 2‐acylaziridines. This sigmatropic process is highly stereoselective and can be induced by simple heating or upon metal‐catalysis activation. Here, we wish to highlight its significance for the synthesis of complex aziridine‐containing targets. More information can be found in the Microreview by S. Tangara, A. Kanazawa and S. Py.
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中文翻译:

封面人物:鲍德温重排:2-酰基氮丙啶的合成(Eur.J.Org.Chem.43 / 2017)

封面人物展示了通过鲍德温重排合成的2-酰基氮丙啶。鲍德温重排已有约五十年的历史,其在有机合成中的潜力一直被低估。这是非常令人惊讶的,因为关键的底物4-异恶唑啉是现成的化合物。掩盖特征说明了热力学上有利的环缩过程,该过程将高反应性的4-异恶唑啉转化为更稳定的2-酰基氮丙啶。这个σ过程是高度立体选择性的,可以通过简单的加热或金属催化活化来诱导。在这里,我们希望强调其对于合成复杂的含氮丙啶的靶标的重要性。可以在S.Tangara,A.Kanazawa和S.Py的Microreview中找到更多信息。
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更新日期:2017-11-10
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