A continuous flow process for the Ireland–Claisen rearrangement

Abstract

Herein, we describe an in-depth study of an enantioselective Ireland–Claisen rearrangement using a continuous flow reactor. The use of this innovative technology led to a rapid reaction at room temperature, enabling the stereocontrolled synthesis of vicinal stereogenic centers with little to no loss in yield or optical purity, in the absence of cryogenic conditions. The reaction scope was examined via the synthesis of several allyl esters, and the results were discussed. The validation and scale-up of the process were also performed.