Palladium-Catalyzed, Enantioselective Desymmetrization of <i>N</i>-Acylaziridines with Indoles
Kinney Van Hecke, Tyler R. Benton, Michael Casper, Dustin Mauldin, Brandon Drake, Jeremy B. Morgan
Abstract
Ring opening reactions of meso-aziridines generate chiral amine derivatives where the control of stereochemistry is possible through enantioselective catalysis. We report the use of a diphosphine–palladium(II) catalyst for the highly enantioselective desymmetrization of N-acylaziridines with indoles. The β-tryptamine products are isolated in moderate to high yield across a range of indole and aziridine substitution patterns. The synthetic utility of β-tryptamine products is demonstrated by conversion to the brominated pyrroloindoline derivative.
Topics & Concepts
DesymmetrizationChemistryEnantioselective synthesisPalladiumCatalysisStereochemistryOrganic chemistryCombinatorial chemistrySynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and Catalysis