Electrochemical reduction of beta-aryldehydroamino acid derivatives

Abstract

[Excerpt] Introduction: The reduction of an isolated double bond is not possible using electrochemical methods, however when the double bond is conjugated with an electron withdrawing group such as a carbonyl it becomes reducible in the accessible potential range [1]. For some years now we have been interested in the synthesis of dehydroamino acid derivatives and in using these compounds as substrates in several types of reactions [2]. As part of this work we have been studying the electrochemical behaviour of dehydroamino acid derivatives. Although there are many reports concerning the chemical reduction of α,β-dehydroamino acids, [3] to the best of our knowledge the electrochemical reduction of β,β-disubstituted dehydroamino acids has not yet been described. Since dehydroamino acids can be considered activated alkenes we decided to study the electrochemical reduction of β,β-diaryldehydroalanines and study the photophysical properties of some of the saturated amino acids prepared and compare them with those of the corresponding β,β-diaryldehydroalanines. [...]