Convergent access to bis-spiroacetals through a Sila-Stetter-ketalization cascade
Jessica Labarre-Lainé1, Redouane Beniazza, Valérie Desvergnes
1Université de Bordeaux , Institut des Sciences Moléculaires, UMR-CNRS 5255 351, cours de la libération, 33405 Talence Cedex, France.
Abstract:
An NHC-catalyzed sila-Stetter reaction between aliphatic acylsilanes and vinylketones bearing silyl ether substituents affords functionalized 1,4-diketones, which upon treatment under acidic conditions leads to the corresponding bis-spiroacetals. The two-step sequence may also be carried out in a one-pot operation leading to high yields of the desired bis-spiroacetals.
Related Concept Videos
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview
Cycloaddition Reactions: Overview
Prochirality
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction


