The Reaction of Organocerium Reagents with Easily Enolizable Ketones

Abstract

Organocerium(III) reagents were conveniently generated by the reaction of organolithium compounds with anhydrous cerium(III) chloride. The reagents are less basic than organolithiums and Grignard reagents, and they react readily at -78°C with easily eno lizable ketones such as 2-tetralone to afford addition products in high yields. Cerium (III) enolates were also generated from lithium enolates and cerium (III) chloride. The cerium (111) e nolates undergo aldol addition with ketones or sterically crowded aldehyde to give the corresponding β-hydroxy ketones in good to high yields.