Litcius/Paper detail

Nickel-catalyzed asymmetric reductive cross-coupling of α-chloroesters with (hetero)aryl iodides

Travis J. DeLano, Sara E. Dibrell, Caitlin R. Lacker, Adam R. Pancoast, Kelsey E. Poremba, Leah Cleary, Matthew S. Sigman, Sarah E. Reisman

2021Chemical Science66 citationsDOIOpen Access PDF

Abstract

An asymmetric reductive cross-coupling of α-chloroesters and (hetero)aryl iodides is reported. This nickel-catalyzed reaction proceeds with a chiral BiOX ligand under mild conditions, affording α-arylesters in good yields and enantioselectivities. The reaction is tolerant of a variety of functional groups, and the resulting products can be converted to pharmaceutically-relevant chiral building blocks. A multivariate linear regression model was developed to quantitatively relate the influence of the α-chloroester substrate and ligand on enantioselectivity.

Topics & Concepts

ArylNickelCatalysisCoupling (piping)Combinatorial chemistryReductive eliminationChemistryCoupling reactionMaterials scienceOrganic chemistryMetallurgyAlkylCatalytic C–H Functionalization MethodsOxidative Organic Chemistry ReactionsAlkaloids: synthesis and pharmacology