Dynamic Kinetic Resolution of Aldehydes by Hydroacylation

Dynamic duo: Racemic α‐allyl aldehydes undergo stereoconvergent hydroacylation to generate α,γ‐disubstituted cyclopentanones with high diastereo‐ and enantioselectivities. In this dynamic kinetic resolution, a primary amine catalyst racemizes the aldehyde substrate via enamine formation and hydrolysis while a rhodium catalyst promotes cyclization.

Abstract

We report a dynamic kinetic resolution (DKR) of chiral 4‐pentenals by olefin hydroacylation. A primary amine racemizes the aldehyde substrate via enamine formation and hydrolysis. Then, a cationic rhodium catalyst promotes hydroacylation to generate α,γ‐disubstituted cyclopentanones with high enantio‐ and diastereoselectivities.

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