87920-11-4Relevant academic research and scientific papers
Conjugate hydroboration-reduction and organolithium additions to acylketene acetals. Synthesis of monoprotected β-dicarbonyls
Eid Jr.,Konopelski
, p. 305 - 306 (1990)
Hydride and organolithium additions to acylketene acetals are presented. Results indicate conjugate addition to be the dominant reaction pathway, resulting in the formation of monoprotected β-diketones and β-ketoaldehydes.
Acylketene acetals in organic synthesis
Eid Jr.,Konopelski
, p. 975 - 992 (2007/10/02)
The preparation and reactivity of achiral and enantiomerically pure acylketene acetals are described. The key reactions of these substrates involve facile conjugate hydroboration and organolithium addition. Enantiomerically pure acylketene acetals were employed to generate a homochiral β-keto ketal through a highly diastereoselective lithium enolate quench. This β-ketal, which was also prepared through a desymmetrization ketalization reaction on a meso dione, was employed in the synthesis of the insect pheromone sitophilure.
