Palladium Catalyzed C-Arylation of Amino Acid Derived Hydantoins

Fernando Fernández-Nieto, Josep Mas Roselló, Simone Lenoir, Simon Hardy, Jonathan Clayden*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

16 Citations (Scopus)

Abstract

Palladium(II) trifluoroacetate (5 mol %) catalyzes the C-arylation of N,N-disubstituted hydantoins by aryl iodides in good yield. The reaction proceeds through base-promoted enolization of the amino acid derived hydantoins, and the resulting 5,5-disubstituted hydantoins may be deprotected at one or both N atoms to yield biologically active structures or alternatively hydrolyzed to the parent α-aryl α-amino acids. The reaction is successful with a variety of parent amino acids and a range of electron-rich and electron-poor aryl iodides.

Original languageEnglish
Pages (from-to)3838-3841
Number of pages4
JournalOrganic Letters
Volume17
Issue number15
Early online date22 Jul 2015
DOIs
Publication statusPublished - 7 Aug 2015

Fingerprint Dive into the research topics of 'Palladium Catalyzed C-Arylation of Amino Acid Derived Hydantoins'. Together they form a unique fingerprint.

  • Projects

    Cite this

    Fernández-Nieto, F., Mas Roselló, J., Lenoir, S., Hardy, S., & Clayden, J. (2015). Palladium Catalyzed C-Arylation of Amino Acid Derived Hydantoins. Organic Letters, 17(15), 3838-3841. https://doi.org/10.1021/acs.orglett.5b01803