cis-Aziridines From Terminal Alkenes via Diastereoselective Intramolecular Electrocatalytic Hydroamination

Area of Science:

• Organic Chemistry
• Catalysis
• Synthetic Methodology

Background:

• Aziridines are crucial synthetic intermediates with significant biological applications.
• Existing methods for synthesizing 2,3-disubstituted aziridines often lack stereochemical predictability and rely on hazardous reagents.
• There is a need for efficient and scalable methods to access stereochemically defined aziridines.

Purpose of the Study:

• To develop a novel, general strategy for the synthesis of cis-2,3-disubstituted aziridines.
• To establish a stereoselective aziridination protocol using readily available starting materials.
• To explore an electrocatalytic approach for aziridine synthesis, avoiding traditional diazo or nitrene chemistry.

Main Methods:

• Electrocatalytic cobalt-catalyzed hydroamination of allylic sulfonamides.
• Mechanistic studies including density functional theory (DFT) analysis.
• Investigation of diastereoselectivity control during radical recombination.

Main Results:

• A scalable protocol for synthesizing cis-2,3-disubstituted aziridines was established.
• The method demonstrates predictable stereochemical outcomes, independent of starting alkene geometry.
• The synthesized cis-aziridines serve as versatile intermediates for further synthetic transformations.

Conclusions:

• The developed electrocatalytic hydroamination offers a safe, efficient, and scalable route to stereochemically enriched cis-aziridines.
• This method overcomes limitations of conventional aziridination techniques.
• The protocol provides valuable functional intermediates for organic synthesis.