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

‘‘Dial up and lock in’’: asymmetric organo-Brønsted acid catalysis incorporating stable isotopes
‘‘Dial up and lock in’’: asymmetric organo-Brønsted acid catalysis incorporating stable isotopes
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.
921-945
Bew, S.P.
d58c5e68-9f12-42a4-8b86-9f443fca53e3
Bachera, Dominika U.
b06593cf-8886-44ed-bd39-6b54ef21b6d8
Coles, Simon
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Hiatt-Gipson, Glyn D.
4b99b424-e433-427f-9c36-a6e1f74f069a
Pesce, Paolo
685df5a6-4bb2-4c96-982c-c63719dc2747
Pitak, Mateusz
eeb6a00f-2291-4376-830f-d30dfd607ed1
Thurston, Sean M.
15544981-5b6e-4cef-b4f8-ad010e415ef4
Zdorichenko, Victor
ab3c4558-d380-4962-af0f-5e23a3ef33c6
Bew, S.P.
d58c5e68-9f12-42a4-8b86-9f443fca53e3
Bachera, Dominika U.
b06593cf-8886-44ed-bd39-6b54ef21b6d8
Coles, Simon
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Hiatt-Gipson, Glyn D.
4b99b424-e433-427f-9c36-a6e1f74f069a
Pesce, Paolo
685df5a6-4bb2-4c96-982c-c63719dc2747
Pitak, Mateusz
eeb6a00f-2291-4376-830f-d30dfd607ed1
Thurston, Sean M.
15544981-5b6e-4cef-b4f8-ad010e415ef4
Zdorichenko, Victor
ab3c4558-d380-4962-af0f-5e23a3ef33c6

Bew, S.P., Bachera, Dominika U., Coles, Simon, Hiatt-Gipson, Glyn D., Pesce, Paolo, Pitak, Mateusz, Thurston, Sean M. and Zdorichenko, Victor (2016) ‘‘Dial up and lock in’’: asymmetric organo-Brønsted acid catalysis incorporating stable isotopes. Chem, 1 (6), 921-945. (doi:10.1016/j.chempr.2016.11.008).

Record type: Article

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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Accepted/In Press date: 16 November 2016
e-pub ahead of print date: 8 December 2016
Published date: 8 December 2016
Organisations: Chemistry, Chemistry Research Support

Identifiers

Local EPrints ID: 406159
URI: http://eprints.soton.ac.uk/id/eprint/406159
PURE UUID: 2402e1bd-a0a2-4657-b445-7abc142cabcd
ORCID for Simon Coles: ORCID iD orcid.org/0000-0001-8414-9272
ORCID for Mateusz Pitak: ORCID iD orcid.org/0000-0002-3680-7100

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Date deposited: 10 Mar 2017 10:40
Last modified: 02 Sep 2020 01:33

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