Enantioselective synthesis of hydantoins by chiral acid-catalysed condensation of glyoxals and ureas.
| Autor: | Aryal S; School of Physical and Chemical Sciences, University of Canterbury Christchurch New Zealand daniel.foley@canterbury.ac.nz., Hone CA; Center for Continuous Flow Synthesis and Processing, Research Center Pharmaceutical Engineering Graz Austria., Polson MIJ; School of Physical and Chemical Sciences, University of Canterbury Christchurch New Zealand daniel.foley@canterbury.ac.nz., Foley DJ; School of Physical and Chemical Sciences, University of Canterbury Christchurch New Zealand daniel.foley@canterbury.ac.nz.; Biomolecular Interaction Centre, University of Canterbury Christchurch New Zealand. |
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| Jazyk: | angličtina |
| Zdroj: | Chemical science [Chem Sci] 2023 Jun 13; Vol. 14 (29), pp. 7905-7912. Date of Electronic Publication: 2023 Jun 13 (Print Publication: 2023). |
| DOI: | 10.1039/d3sc01656k |
| Abstrakt: | Hydantoins are important scaffolds in natural products and pharmaceuticals, with only a few synthetic strategies available for their asymmetric preparation. We herein describe a single-step enantioselective synthesis of 5-monosubstituted hydantoins via condensation of glyoxals and ureas in the presence of a chiral phosphoric acid at room temperature. Products were formed in up to 99% yield and 98 : 2 e.r. Using mechanistic and kinetic studies, including time course 1 H NMR monitoring, we revealed that the reaction likely proceeds via face-selective protonation of an enol-type intermediate. Competing Interests: There are no conflicts to declare. (This journal is © The Royal Society of Chemistry.) |
| Databáze: | MEDLINE |
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