Organic Chemistry

Catalytic Deracemization of α-Branched Aldehydes via Visible Light Promoted E/Z Isomerization of Enamine Intermediate

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Abstract

Catalytic deracemization of α-branched aldehydes represents an unmet challenge with fundamental importance in carbonyl chemistry. In this work, we report a photochemical E/Z isomerization strategy for the deracemization of α-branched aldehydes by using simple aminocatalysts and readily available photosensitizers. Various racemic α-branched aldehydes could be directly transformed into their corresponding single enantiomers in high enantioselectivity. Rapid photodynamic E/Z isomerization and highly stereospecific iminium/enamine tautomerization are two key factors that underlie the highly effective enantio-enrichment. This study presents a distinctive photochemical E/Z isomerizing strategy for externally tuning enamine catalysis.

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Supplementary material

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Catalytic Deracemization of α-Branched Aldehydes via Visible Light Promoted E/Z Isomerization of Enamine Intermediate
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