Biomimetic Catalytic Retro-Aldol Reaction Using a Cation-Binding Catalyst: A Promising Route to Axially Chiral Biaryl Aldehydes

Here we describe a biomimetic catalytic retro-aldol reaction of racemic alpha-substituted beta-hydroxy ketones utilizing a chiral oligoEG cation-binding catalyst as a type-II aldolase mimic. Our investigation of various aldol substrates has demonstrated that our biomimetic retro-aldol protocol enables rapid access to highly enantiomerically enriched aldols with a selectivity factor (s) of up to 70. Additionally, we have demonstrated the synthetic strategy's feasibility for accessing diverse and valuable axially chiral aldehydes.

Automated summary

In this study, a biomimetic catalytic retro-aldol reaction using a chiral oligoEG cation-binding catalyst as a mimic of type-II aldolase was described. The investigation of various aldol substrates showed that our biomimetic retro-aldol protocol allows for rapid access to highly enantiomerically enriched aldols with a selectivity factor (s) of up to 70. Additionally, the feasibility of the synthetic strategy for accessing diverse and valuable axially chiral aldehydes was demonstrated.