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

Angyal, Anikó and Demjén, András and Harmat, Veronika and Wölfling, János and Puskás, László G. and Kanizsai, Iván (2019) 1,3-Dipolar Cycloaddition of Isatin-Derived Azomethine Ylides with 2H‐Azirines: Stereoselective Synthesis of 1,3- Diazaspiro[bicyclo[3.1.0]hexane]oxindoles. JOURNAL OF ORGANIC CHEMISTRY, 84 (7). pp. 4273-4281. ISSN 0022-3263

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Abstract

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.

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