‘‘Dial up and lock in’’: asymmetric organo-Brønsted acid catalysis incorporating stable isotopes

Abstract

An operationally simple organo-Brønsted-acid-catalyzed asymmetric andregioselective ‘‘dial up and lock in’’ of one or more stable isotopes into organiccompounds is unknown. Here, we describe a newly designed, chemically versatileprotocol mediating single- or multiple-isotope incorporation into aziridinesvia a one-pot, three-component, two-step process. By exploiting easy-togenerate isotope-derived starting materials, it allows complete control ofisotope positioning, affords >95 atom % isotope incorporation, and generatescis-aziridines with excellent optical activities and regioselectivities. Demonstrating a ‘‘low entry point,’’ and thus easy access to a broad range of researchers, it requires no specialist laboratory equipment and employs readilyattainable reaction conditions. Demonstrating their utility, the aziridines areeasily transformed into sought-after chiral non-racemic a-amino acids appendedwith one to three (or more) identical or different isotopes. The widespread useof these compounds ensures that our methodology will be of interest to biological, medicinal, pharmaceutical, agrochemical, biotechnology, materials, and process chemists alike.

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Identifiers

ORCID for Simon Coles: orcid.org/0000-0001-8414-9272

ORCID for Mateusz Pitak: orcid.org/0000-0002-3680-7100

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