Formation of All-Carbon Quaternary Centers via Enantioselective Pd-Catalyzed α-Vinylation of γ-Lactams
Farbod A. Moghadam, Jay P. Barbor, Melinda Chan, Carina I. Jette, Shunya Sakurai, Brian M. Stoltz
Abstract
Herein, we report an enantioselective vinylation of α-substituted γ-lactams that forges quaternary centers in up to 59% yield with 94% ee. The use of canonically inactive vinyl chloride electrophiles afforded the highest yields and levels of stereoselectivity, and a range of trisubstituted vinyl chlorides were found to be proficient in promoting this transformation. These stereogenic products could be further elaborated to functionally rich scaffolds, thereby highlighting the synthetic utility of this process.
Topics & Concepts
StereocenterEnantioselective synthesisChemistryElectrophileQuaternary carbonYield (engineering)StereoselectivityCatalysisCombinatorial chemistryChlorideOrganic chemistryMaterials scienceMetallurgyCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and Catalysis