133407-79-1Relevant academic research and scientific papers
Enantiomerically pure ketals in synthesis. Diastereoselective formation of β-keto and β-hydroxy ketals
Eid Jr., Clark N.,Konopelski, Joseph P.
, p. 461 - 464 (2007/10/02)
Enantiomerically pure acylketene acetals were employed to generate a homochiral β-keto ketal through a highly diastereoselective lithium enolate quench. The β-keto ketal, which was also prepared through a desymmetrization ketalization reaction on a meso dione, was employed in the synthesis of the isomers of the insect pheromone sitophilure.
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.
CONJUGATE ADDITION REACTIONS OF ENANTIOMERICALLY PURE ACYLKETENE ACETALS AND ETHYLLITHIUM. A PRONOUNCED SALT EFFECT.
Konopelski, Joseph P.
, p. 465 - 466 (2007/10/02)
The order of addition of salt-free ethylithium/benzene solution to enantiomerically pure acylketene acetal 1 dictates the product formed in a chemospecific manner.Introduction of lithium bromide removes the distinction.
