Ruthenium-Catalyzed Synthesis of 2H‑Azirines from Isoxazolinones

2H-Azirines are synthetically versatile, highly strained, three-membered heterocycles containing an imino double bond. We report their efficient Ru-catalyzed synthesis using low catalyst loadings under neutral conditions from isoxazolinone substrates, which are readily accessible from β-ketoesters....

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Bibliographic Details
Published in:Organic letters 2017-09, Vol.19 (17), p.4436-4439
Main Authors: Rieckhoff, Stefan, Titze, Marvin, Frey, Wolfgang, Peters, René
Format: Article
Language:English
Online Access:Get full text
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Summary:2H-Azirines are synthetically versatile, highly strained, three-membered heterocycles containing an imino double bond. We report their efficient Ru-catalyzed synthesis using low catalyst loadings under neutral conditions from isoxazolinone substrates, which are readily accessible from β-ketoesters. The azirines were shown to be efficient precursors for functionalized pyridine, indole, dihydropyrrole, and pyrrolidine heterocycles.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b01895