Palladium-catalyzed enantioselective three-component synthesis of α-arylglycine derivatives from glyoxylic acid, sulfonamides and aryltrifluoroborates

Beilstein J Org Chem. 2023 May 25:19:719-726. doi: 10.3762/bjoc.19.52. eCollection 2023.

Abstract

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

Keywords: Petasis reaction; amino acids; asymmetric catalysis; multicomponent reaction; palladium catalysis; sulfonamides.

Grants and funding

Financial support by the research unit NanoKat (RPTU Kaiserslautern-Landau) is gratefully acknowledged.