A Telescoped Continuous Flow Enantioselective Process to Access Chiral Intermediates of Atomoxetine, Dapoxetine, Duloxetine and Ezetimibe
Abstract
A telescoped continuous flow process is reported for the enantioselective synthesis of chiral precursors of 1-aryl-1,3-diols, intermediates in the synthesis of Ezetimibe, Dapoxetine, Duloxetine and Atomoxetine. The two-step sequence consists of an asymmetric allylboration of readily available aldehydes using a polymer-supported chiral phosphoric acid catalyst to introduce asymmetry, followed by selective epoxidation of the resulting alkene. The process is highly stable for at least 7 h and represents a transition-metal free enantioselective approach to valuable 1-aryl-1,3-diols.
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