Substrate-Directed Enantioselective Aziridination of Alkenyl Alcohols Controlled by a Chiral Cation

Title	Substrate-Directed Enantioselective Aziridination of Alkenyl Alcohols Controlled by a Chiral Cation
Authors	Alexander Fanourakis, Nicholas J. Hodson, Arthur R. Lit, Robert J. Phipps
Magazine	Journal of the American Chemical Society
Date	03/24/2023
DOI	10.1021/jacs.3c00693
Introduction	Aziridination of alkenes is a versatile transformation used to construct chiral nitrogen-containing compounds. We report an enantioselective aziridination of alkenyl alcohols, enabling asymmetric nitrene transfer to a variety of alkenes. Our method is substrate-directed, utilising non-covalent interactions between the substrate, achiral dianionic rhodium(II,II) tetracarboxylate dimer, and cinchona alkaloid-derived cations, which form a chiral pocket for aziridination. We evaluate compatible alkene classes, present a mnemonic for predicting reaction outcomes, and propose post-functionalisation protocols showcasing the synthetic potential of enantioenriched aziridine-alcohol products.
Quote	A. Fanourakis, N. J. Hodson and A. R. Lit et al. Substrate-Directed Enantioselective Aziridination of Alkenyl Alcohols Controlled by a Chiral Cation. J. Am. Chem. Soc. 2023. Vol. 145(13):7516-7527. DOI: 10.1021/jacs.3c00693
Element	Rhodium (Rh)
Materials	Chemical Compounds
Industry	Chemical & Pharmacy

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