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

Liang, Yujie; Strieth-Kalthoff, Felix; Bellotti, Peter; Glorius, Frank

Abstract

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.