Litcius/Paper detail

Catalytic Enantioselective Reductive Cross Coupling of Electron-Deficient Olefins

Kangning Cao, Chunyang Li, Dong Tian, Xiaowei Zhao, Yanli Yin, Zhiyong Jiang

2022Organic Letters30 citationsDOI

Abstract

We report an enantioselective reductive cross coupling of electron-deficient olefins. Using a visible-light-driven cooperative photoredox and chiral Brønsted acid-catalyzed reaction with a Hantzsch ester as the terminal reductant, various cyclic and acyclic enones with 2-vinylpyridines were converted in high yields (up to 93%) to a wide range of enantioenriched pyridine derivatives featuring diverse γ-tertiary carbon stereocenters with good to excellent enantioselectivities (up to >99% ee).

Topics & Concepts

StereocenterChemistryEnantioselective synthesisCatalysisPyridineBrønsted–Lowry acid–base theoryCombinatorial chemistryCoupling (piping)ElectronOptically activeOrganic chemistryPhysicsEngineeringQuantum mechanicsMechanical engineeringRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsOxidative Organic Chemistry Reactions