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Palladium Catalyzed C-Arylation of Amino Acid Derived Hydantoins.
Org Lett. 2015 Aug 07; 17(15):3838-41.OL

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.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Fernández-Nieto F
†School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, U.K.
Mas Roselló J
†School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, U.K.
Lenoir S
†School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, U.K.
Hardy S
‡Syngenta Ltd., Jealott's Hill Research Centre, Bracknell, Berkshire, RG42 6EY, U.K.
Clayden J
†School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, U.K.

MeSH

Amino AcidsCatalysisHydantoinsHydrocarbons, IodinatedMolecular StructurePalladium

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

26200165

Citation

Fernández-Nieto, Fernando, et al. "Palladium Catalyzed C-Arylation of Amino Acid Derived Hydantoins." Organic Letters, vol. 17, no. 15, 2015, pp. 3838-41.
Fernández-Nieto F, Mas Roselló J, Lenoir S, et al. Palladium Catalyzed C-Arylation of Amino Acid Derived Hydantoins. Org Lett. 2015;17(15):3838-41.
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), 3838-41. https://doi.org/10.1021/acs.orglett.5b01803
Fernández-Nieto F, et al. Palladium Catalyzed C-Arylation of Amino Acid Derived Hydantoins. Org Lett. 2015 Aug 7;17(15):3838-41. PubMed PMID: 26200165.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium Catalyzed C-Arylation of Amino Acid Derived Hydantoins. AU - Fernández-Nieto,Fernando, AU - Mas Roselló,Josep, AU - Lenoir,Simone, AU - Hardy,Simon, AU - Clayden,Jonathan, Y1 - 2015/07/22/ PY - 2015/7/23/entrez PY - 2015/7/23/pubmed PY - 2015/12/15/medline SP - 3838 EP - 41 JF - Organic letters JO - Org Lett VL - 17 IS - 15 N2 - 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. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/26200165/Palladium_Catalyzed_C_Arylation_of_Amino_Acid_Derived_Hydantoins_ DB - PRIME DP - Unbound Medicine ER -