Catalytic asymmetric diaziridination.

Area of Science:

• Organic Chemistry
• Asymmetric Synthesis
• Catalysis

Background:

• Diaziridines are strained nitrogen heterocycles with limited synthetic accessibility.
• Existing methods for diaziridine synthesis often lack stereocontrol and efficiency.

Purpose of the Study:

• To develop the first catalytic enantioselective and diastereoselective synthesis of diaziridines.
• To create optically active diaziridines with orthogonally protected nitrogen atoms.

Main Methods:

• Asymmetric phase-transfer catalysis was employed for the aziridination of N-tosyl aldimines.
• A modified hydroxylamine reagent was utilized in the catalytic process.

Main Results:

• The synthesis successfully furnished optically active diaziridines.
• Products were obtained as single diastereomers with high enantiomeric excess (up to 96% ee).
• The synthesized diaziridines possess two orthogonal N-protecting groups amenable to selective deprotection.

Conclusions:

• This work establishes a groundbreaking catalytic method for stereoselective diaziridine synthesis.
• The developed methodology provides access to valuable chiral building blocks with versatile protecting group strategies.