Escot, Lorena;
Gonzalez-Granda, Sergio;
Méndez-Sánchez, Daniel;
Wang, Yu;
Hailes, Helen;
Lavandera, Ivan;
Gotor-Fernández, Vicente;
(2024)
β,β-Disubstituted Alkan-2-ones from Propargylic Alcohols Combining a Meyer-Schuster Rearrangement and Asymmetric Alkene Bioreduction.
Advanced Synthesis & Catalysis
, 366
(22)
pp. 4737-4746.
10.1002/adsc.202400653.
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Abstract
The combination of a gold(I) N-heterocyclic carbene complex and an ene-reductase (ERED) has made possible the synthesis of enantiopure β,β-disubstituted ketones in a one-pot concurrent approach. The protocol consists of the Meyer-Schuster rearrangement of racemic propargylic tertiary alcohols using [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]-[bis(trifluoromethanesulfonyl)-imide]gold(I) (IPrAuNTf2), followed by an asymmetric alkene reduction of the α,β-unsaturated ketone intermediate using the Zymomonas mobilis ERED (NCR-ERED). The chemoenzymatic cascade was optimised with a model substrate, where E/Z-isomers both generated the (R)-ketone, which was rationalised using in silico molecular docking experiments. The cascade was then applied towards the production of a series of (R)-4-substituted-alkan-2-ones in enantiopure form in a straightforward manner.
| Type: | Article |
|---|---|
| Title: | β,β-Disubstituted Alkan-2-ones from Propargylic Alcohols Combining a Meyer-Schuster Rearrangement and Asymmetric Alkene Bioreduction |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1002/adsc.202400653 |
| Publisher version: | http://dx.doi.org/10.1002/adsc.202400653 |
| Language: | English |
| Additional information: | Copyright © 2024 The Author(s). This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
| UCL classification: | UCL UCL > Provost and Vice Provost Offices > UCL BEAMS UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry |
| URI: | https://discovery-pp.ucl.ac.uk/id/eprint/10198059 |
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