Related Experiment Video
Updated: Jun 9, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Copper-Catalyzed Enantioconvergent Radical C(sp3)-N Cross-Coupling to Access Chiral α-Amino-β-lactams
Jing-Jing Zheng1,2, Wei-Long Liu1,2, Qiang-Shuai Gu3
1Shenzhen Key Laboratory of Cross-Coupling Reactions, Southern University of Science and Technology, Shenzhen 518055, China.
Abstract:
A copper-catalyzed enantioconvergent radical C(sp3)-N cross-coupling of racemic tertiary α-bromo-β-lactams with aromatic amines is developed under mild thermal reaction conditions. The use of a sterically demanded oxazoline-derived sulfonamide N,N,N-ligand is crucial for the reaction initiation and effective enantio-discrimination of the azetidinone-derived cyclic alkyl radicals. The strategy provides an attractive approach to access chiral α-amino-β-lactams, an important structural motif in many biologically active molecules. Preliminary mechanistic studies support the formation of azetidinone-derived alkyl radicals from the L*Cu(I)-amido complex and α-bromo-β-lactams.
More Related Videos
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
09:14Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Related Concept Videos
Radical Halogenation: Stereochemistry
Halogenation to form a new chiral center:
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...
Radical Anti-Markovnikov Addition to Alkenes: Overview
α-Alkylation of Ketones via Enolate Ions
Radical Substitution: Allylic Bromination
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction