The formation of aziridines resulting from the addition of a nitrene to an alkene is a well-established synthetic strategy for the stereoselective incorporation of nitrogen. However, the stereoselective synthesis of aziridines from unactivated alkenes remains a challenging transformation. Herein we report the development of an enantioselective aziridination methodology targeting terminal unactivated alkenes. Utilizing a hydroxylamine nitrene source and planar chiral Rh(III) indenyl catalyst a wide range of terminal unactivated alkenes can be converted into enantioenriched aziridines in good yields. The proposed mechanism for this reaction proceeds through a high valent Rh(V) nitrenoid species.

Planar chiral Rh(III) indenyl catalyzed enantioselective aziridination of unactivated terminal alkenes

Where thousands of chemistry professionals meet to share ideas and advance scientific and technical knowledge. Spring 2023 abstracts, posters, and presentations will launch at the end of March.

ACS Spring 2023

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.