Construction of three contiguous stereocenters through amine-catalyzed asymmetric aldol reactions

Three contiguous stereocenters were constructed by an amino acid-catalyzed asymmetric aldol reaction of alpha-siloxyketones with racemizable alpha-haloaldehydes via dynamic kinetic resolution. One-pot catalytic asymmetric synthesis of the highly functionalized products could also be accomplished by the alpha-bromination of simple aldehydes and the subsequent asymmetric aldol reaction.

Automated summary

Three contiguous stereocenters were formed through an amino acid-catalyzed asymmetric aldol reaction between alpha-siloxyketones and racemizable alpha-haloaldehydes via dynamic kinetic resolution. The highly functionalized products can also be synthesized in a one-pot catalytic asymmetric manner by alpha-bromination of simple aldehydes followed by the asymmetric aldol reaction.