1,3- cis -Disubstituted Cycloalkanes by Iridium-Catalyzed Enantio-convergent Migratory Hydroheteroarylation

Abstract

Enantioenriched 1,3-disubstituted cycloalkanes are important structural motifs in pharmaceuticals and natural products, yet their stereoselective synthesis remains challenging owing to difficulties in remote control of regio- and stereoselectivities. Herein, we report an iridium-catalyzed enantio-convergent hydroheteroarylation of racemic unactivated cyclic alkenes through a dynamic kinetic asymmetric transformation (DYKAT). Racemic cyclohexenes, cycloheptenes, and cyclooctenes undergo hydroheteroarylation with excellent regio-, diastereo-, and enantioselectivity, providing 1,3-cis-disubstituted cycloalkanes in an enantio-convergent manner. The method enables the efficient construction of both tertiary–tertiary and quaternary–tertiary stereogenic relationships within saturated carbocyclic frameworks.