Stereodivergent dehydrative allylation of β-keto esters using a Ru/Pd synergistic catalyst.

ABSTRACT: α-Alkylation of a β-keto ester is a frequently used reaction for carbon-carbon bond formation. However, extension to a stereoselective reaction remains a significant challenge, because the product easily racemizes under acidic or basic conditions. Here, we report a hybrid system consisting of Pd and Ru complexes that catalyzes the asymmetric dehydrative condensation between cinnamyl-type allylic alcohols and β-keto esters. α-Non-substituted β-keto ester can be allylated to afford an α-mono-substituted product with high regio-, diastereo-, and enantioselectivity. No epimerization occurs owing to the nearly neutral conditions, which is achieved by a rapid proton transfer from Pd-enolate formation to Ru π-allyl complex formation. Four diastereomers can be synthesized on demand by changing the

SUBMITTER: Le TP 

PROVIDER: S-EPMC9556617 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature