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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SYNLETT Unexpected inversion of configuration during the carbamoylation of 1-azaflavaglines.pdf (1.23 Mo)
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