Catalytic one-carbon homologation of α-amino acids to β-amino aldehydes

The development of a catalytic strategy for one-carbon homologation is of foundational importance in organic synthesis enabling quick elaboration of useful molecules. Herein, we report a dual nickel/photoredox catalytic strategy for transforming a range of α-amino acids into β-amino aldehydes in a simple one-step operation. This method provides a new catalytic blueprint for one-carbon homologation of α-amino acids without requiring any pre-functionalization step and could be strategically important for streamlining the preparation of value-added β-amino aldehydes, versatile building blocks applied in a variety of synthetic transformations. More broadly, mechanistic studies demonstrated here show how a radical generated in situ can be captured for rapid access of aldehydes, which would promote the applications of numerous other molecules for valuable aldehyde synthesis. • Catalytic strategy for direct one-carbon homologation reaction • Streamlining synthesis of valuable β-amino aldehydes from α-amino acids • Mild and operationally simple reaction conditions β-Amino aldehydes are direct precursors of β-amino acids, which are key structural elements of β-peptides. Besides, they have also found wide applications in elaboration of pharmaceutical derivatives and natural products. An important way to prepare β-amino aldehydes is the one-carbon homologation of readily available α-amino acids. However, previous methods typically require a multi-step synthetic procedure or the use of a stoichiometric harsh oxidant, which limits their application. In this article, a dual nickel/photoredox catalytic strategy that enables the streamlining synthesis of β-amino aldehydes from α-amino acids is realized. The reaction proceeds smoothly under mild and operationally simple conditions. The development of a catalytic strategy for one-carbon homologation is of foundational importance in organic synthesis, allowing for quick elaboration of useful molecules. In this article, a dual nickel/photoredox catalytic strategy for transforming a range of abundant biomass α-amino acids into value-added β-amino aldehydes in a simple one-step operation is demonstrated. The reaction proceeds smoothly under mild and operationally simple conditions.