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Didier, Dorian; Music, Arif; Hoarau, Clement; Hilgert, Nicolas; Zischka, Florian (2018): Catalyst-Free Enantiospecific Olefination with in-situ Generated Organocerium Species. In: Angewandte Chemie-international Edition
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Abstract

Described is the in-situ formation of triorganocerium reagents and their implications in catalyst-free Zweifel olefinations. These unique cerium species were generated through novel exchange reactions of organo-halides with n-Bu3Ce reagents. The adequate electronegativity of cerium allowed for compensating both disadvantages of usually functional group sensitive organolithium species and less reactive organomagnesium reagents. Exchange reactions were performed on aryl and alkenyl bromides, enabling enantiospecific transformations of chiral boron pinacol esters. Finally, these new organocerium species were engaged in selective 1,2-additions onto enolizable and sterically hindered ketones.