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Issue 4, 2018
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Synthesis of unnatural α-amino acid derivatives via selective o-C–H functionalization

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Abstract

Pd-Catalyzed o-C–H functionalization of α-phenylglycine, 4-hydroxyphenylglycine and phenylalanine using picolinamide as a directing group is reported. We have developed different protocols for the arylation, alkylation, alkynylation, halogenation, alkoxylation, and acyloxylation of these amino acids. The reactions exhibit high selectivity, broad substrate scope, and compatibility with different functional groups in moderate to high yields. They provide a rapid and efficient access to a variety of phenyl based amino acid derivatives which can be further modified and have broad spectrum of applications in medicinal chemistry.

Graphical abstract: Synthesis of unnatural α-amino acid derivatives via selective o-C–H functionalization

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Publication details

The article was received on 27 Nov 2017, accepted on 19 Dec 2017 and first published on 19 Dec 2017


Article type: Paper
DOI: 10.1039/C7OB02921G
Citation: Org. Biomol. Chem., 2018,16, 598-608
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    Synthesis of unnatural α-amino acid derivatives via selective o-C–H functionalization

    W. Zeng, M. Nukeyeva, Q. Wang and C. Jiang, Org. Biomol. Chem., 2018, 16, 598
    DOI: 10.1039/C7OB02921G

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