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  • Enantioselective Aziridination of Unactivated Terminal Alkenes Using a Planar Chiral Rh(III) Indenyl Catalyst

    • Enantioselective Aziridination of Unactivated Terminal Alkenes Using a Planar Chiral Rh(III) Indenyl Catalyst

    Title Enantioselective Aziridination of Unactivated Terminal Alkenes Using a Planar Chiral Rh(III) Indenyl Catalyst
    Authors Patrick Gross, Hoyoung Im, David Laws III, Bohyun Park, Mu-Hyun Baik, Simon B. Blakey
    Magazine Journal of the American Chemical Society
    Date 01/03/2024
    DOI 10.1021/jacs.3c10637
    Introduction Chiral aziridines are vital structures in natural products and target molecules, serving as key intermediates for synthesising chiral amines. Although advancements in catalyst design have supported enantioselective aziridination of activated olefins, simple and abundant alkyl-substituted olefins remain challenging. This study presents a novel method using a planar chiral rhodium indenyl catalyst to achieve enantioselective aziridination of unactivated alkenes. The transformation demonstrates significant functional group tolerance and excellent chemoselectivity, favouring unactivated over activated alkenes, producing a variety of enantioenriched high-value chiral aziridines. Computational studies reveal a stepwise mechanism where alkene migratory insertion is central, forming a strained four-membered metallacycle, serving as both enantio- and rate-determining steps in the reaction.
    Quote Patrick Gross, Hoyoung Im and David Laws et al. Enantioselective Aziridination of Unactivated Terminal Alkenes Using a Planar Chiral Rh(III) Indenyl Catalyst. J. Am. Chem. Soc. 2024. Vol. 146(2):1447-1454. DOI: 10.1021/jacs.3c10637
    Element Rhodium (Rh)
    Materials Chemical Compounds
    Industry Chemical & Pharmacy
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