1,3-Dipolar Cycloaddition of Isatin-Derived Azomethine Ylides with 2H‑Azirines: Stereoselective Synthesis of 1,3-Diazaspiro[bicyclo[3.1.0]hexane]oxindoles

A regio- and diastereoselective 1,3-dipolar cycloaddition of 2H-azirines with azomethine ylides generated in situ from isatins and α-amino acids has been elaborated, affording an unprecedented aziridine-fused spiro­[imidazolidine-4,3′-oxindole] framework. This one-pot three-component reaction tolera...

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Bibliographic Details
Published in:Journal of organic chemistry 2019-04, Vol.84 (7), p.4273-4281
Main Authors: Angyal, Anikó, Demjén, András, Harmat, Veronika, Wölfling, János, Puskás, László G, Kanizsai, Iván
Format: Article
Language:English
Online Access:Get full text
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Summary:A regio- and diastereoselective 1,3-dipolar cycloaddition of 2H-azirines with azomethine ylides generated in situ from isatins and α-amino acids has been elaborated, affording an unprecedented aziridine-fused spiro­[imidazolidine-4,3′-oxindole] framework. This one-pot three-component reaction tolerates a wide range of substrates and enables the construction of highly diverse 1,3-diazaspiro­[bicyclo[3.1.0]­hexane]­oxindoles in isolated yields up to 81% under mild conditions.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b00242