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Palladium-Catalyzed Enantioselective Three-Component Synthesis of alpha-Arylglycine Derivatives from Glyoxylic Acid, Sulfonamides and Aryl Trifluoroborates

Abstract

A palladium-catalyzed enantioselective three-component reaction of glyoxylic acid, sulfonamides and aryl trifluoroborates is described. This process provides modular access to the important alpha-arylglycine motif in moderate to good yields and enantioselectivies. The formed alpha-arylglycine products constitute useful building blocks for the synthesis of peptides or arylglycine-containing natural products.

Content

Supplementary material

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

Version History

Mar 16, 2023 Version 1

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The content is available under CC BY NC ND 4.0 License CreativeCommons.org [opens in a new tab]

DOI

10.26434/chemrxiv-2023-cfv7c
D O I: 10.26434/chemrxiv-2023-cfv7c [opens in a new tab]

Funding

Forschungsinitiative Rheinland-Pfalz
Research Unit NanoKat

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) have declared ethics committee/IRB approval is not relevant to this content

Keywords

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

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This content is an early or alternative research output and has not been peer-reviewed at the time of posting.