Carbolithiation of S-Alkenyl-N-aryl Thiocarbamates: Carbanion Arylation in a Connective Route to Tertiary Thiols.
Fiche publication
Date publication
mai 2013
Auteurs
Membres identifiés du Cancéropôle Est :
Dr BERBER Hatice
Tous les auteurs :
Castagnolo D, Foley DJ, Berber H, Luisi R, Clayden J
Lien Pubmed
Résumé
S-Alkenyl-N-arylthiocarbamates are formed from allylic alcohols by sigmatropic rearrangement and isomerization or C=C bond cleavage. They undergo carbolithiation with a range of organolithium reagents, generating benzyllithium intermediates in a stereospecific manner which may undergo N to C aryl migration to yield thiocarbamates with tertiary substituents. A simple base-promoted alcoholysis reveals a series of hindered tertiary thiols with branched carbon skeletons.
Référence
Org Lett. 2013 May 3;15(9):2116-9