Enantioselective Hydroesterificative Cyclization of 1,6-Enynes to Chiral γ-Lactams Bearing a Quaternary Carbon Stereocenter
Xinyi Ren, Lin Tang, Chaoren Shen, Huimin Li, Peng Wang, Kaiwu Dong
Abstract
A palladium-catalyzed asymmetric hydroesterification-cyclization of 1,6-enynes with CO and alcohol was developed to efficiently prepare a variety of enantioenriched γ-lactams bearing a chiral quaternary carbon center and a carboxylic ester group. The approach featured good to high chemo-, region-, and enantioselectivities, high atom economy, and mild reaction conditions as well as broad substrate scope. The correlation between the multiple selectivities of such process and the N-substitutes of the amide linker in the 1,6-enyne substrate has been depicted by the crystallographic evidence and control experiments.
Topics & Concepts
StereocenterChemistryEnantioselective synthesisEnyneSubstrate (aquarium)AmideCatalysisCombinatorial chemistryAtom economyLinkerQuaternary carbonStereochemistryOrganic chemistryOperating systemOceanographyGeologyComputer scienceSynthetic Organic Chemistry MethodsCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and Catalysis