Chiral oxazolidinones via biocatalytic aziridination of unactivated alkenes.

Haemprotein-catalyzed aziridination enables enantioselective synthesis of chiral oxazolidinones from unactivated alkenes, achieving high stereoselectivity in a single step.

• Why it matters: Chiral oxazolidinones are vital in asymmetric synthesis and drug development, especially for antibiotics targeting resistant Mycobacterium tuberculosis. Current methods struggle to efficiently install the 5-stereocenter, limiting access to these compounds.
• What they did: The researchers developed a haemprotein-catalyzed aziridination/ring-expansion cascade, using directed evolution to introduce mutations that facilitate enantioselective functionalization of simple, unactivated alkenes, a reactivity previously limited to conjugated systems.
• The result: This approach provides a direct, enantioselective route to clinically relevant oxazolidinones, expanding the toolkit for asymmetric synthesis and enabling new avenues in antibiotic development.