METALLATION ET ALKYLATION DES THIOIMIDOESTERS: APPLICATION EN SYNTHESE

Article abstract of DOI:10.1016/S0040-4020(01)91806-X

Alkylation of delocalized anions resulting from metallation of N-phenyl thioimidoesters (precursors of dithioesters and thiolesters) takes place on nitrogen with "saturated" thioimidoesters (alkane thiomidates).On the contrary, unsaturated thiomidoesters (α or β-ethylenic, α-arylated) are regioselectively alkylated on the α carbon atom by alkyl or allylic halides.The possibilities for synthesis offered by successive uses of the reactivities of thioimidoester and dithioester functions (allowing in particular two electrophilic additions on two vicinal carbons) are illustrated by syntheses of terpenic compounds lavandual (and lavandulol) and ar-curcumene.