Deracemization through photochemical <i>E</i> / <i>Z</i> isomerization of enamines
Mouxin Huang, Long Zhang, Tianrun Pan, Sanzhong Luo
Abstract
Catalytic deracemization of α-branched aldehydes is a direct strategy to construct enantiopure α-tertiary carbonyls, which are essential to pharmaceutical applications. Here, we report a photochemical E / Z isomerization strategy for the deracemization of α-branched aldehydes by using simple aminocatalysts and readily available photosensitizers. A variety of racemic α-branched aldehydes could be directly transformed into either enantiomer with high selectivity. Rapid photodynamic E / Z isomerization and highly stereospecific iminium/enamine tautomerization are two key factors that underlie the enantioenrichment. This study presents a distinctive photochemical E / Z isomerization strategy for externally tuning enamine catalysis.