Asymmetric Synthesis of Quaternary Hydantoins via a Palladium-Catalyzed Aza-Heck Cyclization
Date
2025-11-14
Journal Title
Journal ISSN
Volume Title
Publisher
Journal of the American Chemical Society
Abstract
An asymmetric, palladium-catalyzed aza-Heck cyclization to prepare enantioenriched 5,5-disubstituted hydantoins (quaternary hydantoins), which are medicinally important compounds but are classically challenging to prepare, is reported. The required substrates can be prepared readily from α,β-unsaturated amides in a single operation, and aza-Heck cyclization provides a wide range of topologically complex, highly substituted, pharmaceutically relevant hydantoins. The capacity of this method to impact the synthesis of drug substances is demonstrated by the first asymmetric synthesis of the anticonvulsant (R)-mephenytoin.
Description
This article was originally published in Journal of the American Chemical Society . The version of record is available at: https://pubs.acs.org/doi/10.1021/jacs.5c16022
This publication is licensed under CC-BY 4.0 https://creativecommons.org/licenses/by/4.0/
© 2025 The Authors. Published by American Chemical Society
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Citation
Meck, E. A., Omer, H. M., Edwards, M. J., Idowu, T. D., Murray, M. L., Korch, K. M., & Watson, D. A. (2025). Asymmetric Synthesis of Quaternary Hydantoins via a Palladium-Catalyzed Aza-Heck Cyclization. Journal of the American Chemical Society.https://doi.org/10.1021/jacs.5c1602