Related Experiment Video
Updated: Aug 20, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Photocatalytic Alkyl Addition to Access Quaternary Alkynyl α-Amino Esters
Juyeong Kim1,2, Jae Kyun Lee1, Bongjin Moon2
1Brain Science Institute, Korea Institute of Science and Technology, Seoul 02792, Republic of Korea.
Abstract:
A regioselective alkylation of β,γ-alkynyl-α-imino esters by visible-light photocatalysis has been developed. This method enables 1,2-addition of methyl, primary, secondary, and tertiary alkyl radicals to the conjugated imines under mild conditions to produce a variety of quaternary alkynyl α-amino acid and cyclic amino acid motifs. Alkyl radicals are generated from alkyl bis(catecholato)silicates with an organic photocatalyst. This process is effective under an air atmosphere, providing operational benefits compared to conventional alkylation using organometallic reagents.
Related Concept Videos
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Acid Halides to Esters: Alcoholysis
Electrophilic Addition to Alkynes: Halogenation
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
Aldol Condensation with β-Diesters: Knoevenagel Condensation
Conjugate Addition to α,β-Unsaturated Carbonyl Compounds

