Cover Feature: The Baldwin Rearrangement: Synthesis of 2‐Acylaziridines (Eur. J. Org. Chem. 43/2017). Issue 43 (10th November 2017)

• Record Type: Journal Article
• Authors: Tangara, Salia; Kanazawa, Alice; Py, Sandrine
• Is Part Of: European journal of organic chemistry. Issue 43(2017)
• Page Start: 6355
• Page End: 6355
• Publication Date: 2017-11-10
• Subjects: Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201701548
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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 theMicroreview by S. Tangara, A. Kanazawa and S. Py .