6 research outputs found
Alpha-Alkylidenecyclopentanones by Alpha-Alkylidation of Methyl 2-Oxocyclopentanecarboxylate
An α-alkylidation of cyclopentanone was achieved in two reaction steps in an overall yield of 20 to 79% via a zinc chloride-catalyzed thioalkylation of the zinc enolate of methyl 2-oxocyclopentanecarboxylate (3) and subsequent saponification/desulfurization of the β-(phenylthio) ketone intermediates 5. For the saponificatioddesuiurization step DABCO proved to be the reagent of choice and superior to the use of alkali or magnesium halides