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Article Dans Une Revue SYNLETT Année : 2020

Unexpected Inversion of Configuration During the Carbamoylation of 1-Azaflavaglines

Résumé

Abstract The acylation of 8-demethoxy-1-azaflavaglines by dimethylcarbamoyl chloride was found to operate with an inversion of configuration, which is rationalized by the occurrence of styrylurea intermediate. The configuration-reversed products were not observed when the substrate was substituted by a methoxy in position 8, suggesting that an overstabilization of the carbocationic intermediate prevents this reaction to take place.

Domaines

Chimie organique
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Dates et versions

hal-03373324 , version 1 (11-10-2021)

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Hussein Abou-Hamdan, Laurent Désaubry. Unexpected Inversion of Configuration During the Carbamoylation of 1-Azaflavaglines. SYNLETT, 2020, 31 (20), pp.2023-2026. ⟨10.1055/s-0040-1707277⟩. ⟨hal-03373324⟩

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