One-Pot Chemoenzymatic Cascade for the Enantioselective C(1)-Allylation of Tetrahydroisoquinolines
Jack J. Sangster, Rebecca E. Ruscoe, Sebastian C. Cosgrove, Juan Mangas‐Sánchez, Nicholas J. Turner
Abstract
Herein, we report a one-pot, chemoenzymatic process for the synthesis of enantioenriched C(1)-allylated tetrahydroisoquinolines. This transformation couples a monoamine oxidase (MAO-N)-catalyzed oxidation with a metal catalyzed allylboration, followed by a biocatalytic deracemization to afford allylic amine derivatives in both high yields and good to high enantiomeric excess. The cascade is operationally simple, with all components added at the start of the reaction and can be used to generate key building blocks for further elaboration.
Topics & Concepts
ChemistryEnantioselective synthesisCascadeCatalysisAmine gas treatingEnantiomerPictet–Spengler reactionOrganic chemistryCombinatorial chemistryEnantiomeric excessCascade reactionAllylic rearrangementChromatographyEnzyme Catalysis and ImmobilizationAsymmetric Hydrogenation and CatalysisChemical synthesis and alkaloids