Picolinamide-directed palladium(II)-catalyzed regioselective hydroacyloxylation of unactivated alkenes.

Abstract

A method for the palladium(II)-catalyzed highly regioselective hydroacyloxylation of unactivated alkenes with carboxylic acids is described using a picolinamide directing group via a Wacker-type nucleopalladation pathway. This novel strategy paves the way for generating very useful β-amino alcohols and esters from simple starting materials, which are important building blocks in many natural products and biologically active compounds. The transformation affords the desired products in good yields and exhibits broad compatibility with aromatic, aliphatic, and fatty carboxylic acids. In addition to forming valuable C-O bonds, the reaction generates a new stereogenic center, providing a synthetically valuable platform for further functionalization and diversification.