Palladium-Catalyzed Asymmetric Three-Component Reaction between Glyoxylic Acid, Sulfonamides and Arylboronic Acids for the Synthesis of alpha-Arylglycine Derivatives

14 February 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

A palladium-catalyzed asymmetric three-component synthesis of alpha-arylglycine derivatives starting from glyoxylic acid, sulfonamides and arylboronic acids is reported. This novel, operationally simple method offers access to the alpha-arylglycine scaffold in good yields and enantioselectivities. The utilization of a tailored catalyst system enables the enantioselective synthesis of the desired alpha-arylglycines despite a fast racemic background reaction. The obtained products can be directly employed as building blocks in peptide synthesis.

Keywords

Palladium-catalysis
asymmetric catalysis
amino acids
multicomponent reaction
Petasis reaction
sulfonamides
boronic acids

Supplementary materials

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Supporting Information
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Experimental procedures, analytical data and copies of NMR spectra and HPLC chromatograms
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