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; Demjén, András; Harmat, Veronika; Wölfling, János; Puskás, László G.; Kanizsai, Iván

doi:10.1021/acs.joc.9b00242.s003

jo9b00242_si_003.pdf (4.07 MB)

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 contribution

posted on 2019-03-12, 00:00 authored by Anikó Angyal, András Demjén, Veronika Harmat, János Wölfling, László G. Puskás, Iván Kanizsai

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.

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

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