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Mono-selective β-C–H arylation of N-methylated amino acids and peptides promoted by 2-(methylthio)aniline directing group

Abstract

2-(Methylthio)aniline (MTA) directed C(sp3)–H functionalisations are efficient and straightforward protocols for the selective β-modification of N-methylated amino acids. The decreased reactivity of MTA in comparison to the 8-amino¬quinoline (AQ) directing group allows for selective monoarylations in high yields without the formation of side products. The protocol is also suitable for the introduction of highly functionalised side chains onto C-terminal alanines of dipeptides. The MTA directing group can easily be removed, providing the free carboxylic acids as valuable building blocks.

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Publication details

The article was accepted on 14 May 2019 and first published on 14 May 2019


Article type: Paper
DOI: 10.1039/C9OB00966C
Org. Biomol. Chem., 2019, Accepted Manuscript

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    Mono-selective β-C–H arylation of N-methylated amino acids and peptides promoted by 2-(methylthio)aniline directing group

    T. Kinsinger and U. Kazmaier, Org. Biomol. Chem., 2019, Accepted Manuscript , DOI: 10.1039/C9OB00966C

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