Diastereoselective Alkene Hydroesterification Enabling the Synthesis of Chiral Fused Bicyclic Lactones

Abstract

Palladium‐catalysed diastereoselective hydroesterification of alkenes assisted by the coordinative hydroxyl group in the substrate afforded a variety of chiral γ‐butyrolactones bearing two stereocenters. Employing the carbonylation‐lactonization products as the key intermediates, the route from the alkenes with single chiral center to chiral THF‐fused bicyclic γ‐lactones containing three stereocenters was developed.

Pd-Catalyzed Enantioselective Hydroamidocarbonylation of α-Substituted Acrylamides to Chiral Succinimides

“…Recently, the carbonyl substituents in alkene substrates were utilized to improve the activity and enantioselectivity of Pd-catalyzed asymmetric hydrocarbonylations . These reactions efficiently delivered various optically active succinic acids and their derivatives, which could be readily transformed into a diverse array of chiral heterocycles. , Among these reported protocols, the asymmetric hydroxycarbonylation of α-methylene-γ-amide carboxylic acids followed by intermolecular condensation between the amide group and the carboxylic acid could afford chiral 2-substituted succinimides, but neither of the imide carbonyl groups was contributed from the implanted CO group.…”