Open Access
Enantioselective synthesis of hydantoins by chiral acid-catalysed condensation of glyoxals and ureas
2
Center for Continuous Flow Synthesis and Processing, Research Center Pharmaceutical Engineering, Graz, Austria
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Publication type: Journal Article
Publication date: 2023-06-13
scimago Q1
wos Q1
SJR: 2.138
CiteScore: 12.6
Impact factor: 7.4
ISSN: 20416520, 20416539
PubMed ID:
37502327
General Chemistry
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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12
Total citations:
12
Citations from 2025:
3
(25%)
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MLA
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GOST
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Aryal S. et al. Enantioselective synthesis of hydantoins by chiral acid-catalysed condensation of glyoxals and ureas // Chemical Science. 2023. Vol. 14. No. 29. pp. 7905-7912.
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Aryal S., Hone C. A., Polson M. I. J., Foley D. J. Enantioselective synthesis of hydantoins by chiral acid-catalysed condensation of glyoxals and ureas // Chemical Science. 2023. Vol. 14. No. 29. pp. 7905-7912.
Cite this
RIS
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TY - JOUR
DO - 10.1039/d3sc01656k
UR - https://xlink.rsc.org/?DOI=D3SC01656K
TI - Enantioselective synthesis of hydantoins by chiral acid-catalysed condensation of glyoxals and ureas
T2 - Chemical Science
AU - Aryal, Sushant
AU - Hone, Christopher A
AU - Polson, Matthew I. J.
AU - Foley, Daniel J
PY - 2023
DA - 2023/06/13
PB - Royal Society of Chemistry (RSC)
SP - 7905-7912
IS - 29
VL - 14
PMID - 37502327
SN - 2041-6520
SN - 2041-6539
ER -
Cite this
BibTex (up to 50 authors)
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@article{2023_Aryal,
author = {Sushant Aryal and Christopher A Hone and Matthew I. J. Polson and Daniel J Foley},
title = {Enantioselective synthesis of hydantoins by chiral acid-catalysed condensation of glyoxals and ureas},
journal = {Chemical Science},
year = {2023},
volume = {14},
publisher = {Royal Society of Chemistry (RSC)},
month = {jun},
url = {https://xlink.rsc.org/?DOI=D3SC01656K},
number = {29},
pages = {7905--7912},
doi = {10.1039/d3sc01656k}
}
Cite this
MLA
Copy
Aryal, Sushant, et al. “Enantioselective synthesis of hydantoins by chiral acid-catalysed condensation of glyoxals and ureas.” Chemical Science, vol. 14, no. 29, Jun. 2023, pp. 7905-7912. https://xlink.rsc.org/?DOI=D3SC01656K.