Electrochemical oxidation of 2-substituted piperidines as a key step towards the synthesis of hydroxylated γ-amino acids

Abstract

2-Substituted piperidines containing different oxygenated side chain functionalities were investigated in the electrochemical, anodic methoxylation. Surprisingly, the configuration of the side chain has a strong influence on the outcome of the electrochemical oxidation. Subsequent elimination of methanol from the oxidation products leads to N-protected eneamides, which upon ozonolysis can be converted to N,N-bisprotected γ-amino aldehydes that are useful building blocks for further synthetic transformations.