Enantioselective synthesis of hydantoins by chiral acid-catalysed condensation of glyoxals and ureas?
Chemical Science Pub Date: 2023-06-13 DOI: 10.1039/D3SC01656K
Abstract
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 1H NMR monitoring, we revealed that the reaction likely proceeds via face-selective protonation of an enol-type intermediate.
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Journal Name：Chemical Science
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CAS no.: 89640-58-4
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