Jump to main content
Jump to site search

Issue 22, 2019
Previous Article Next Article

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

Author affiliations

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 with the 8-aminoquinoline (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 the C-terminal alanines of dipeptides. The MTA directing group can easily be removed, providing free carboxylic acids as valuable building blocks.

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 26 Apr 2019, accepted on 14 May 2019 and first published on 14 May 2019


Article type: Paper
DOI: 10.1039/C9OB00966C
Org. Biomol. Chem., 2019,17, 5595-5600

  •   Request permissions

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

    T. Kinsinger and U. Kazmaier, Org. Biomol. Chem., 2019, 17, 5595
    DOI: 10.1039/C9OB00966C

Search articles by author

Spotlight

Advertisements