Related Experiment Video
Updated: Sep 7, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Catalytic Enantioselective Reductive Cross Coupling of Electron-Deficient Olefins
Kangning Cao1,2, Chunyang Li2, Dong Tian2
1College of Advanced Interdisciplinary Science and Technology, Henan University of Technology, Zhengzhou, Henan 450001, P. R. China.
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).
Related Concept Videos
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Reduction of Alkenes: Catalytic Hydrogenation
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

