Synthesis of β-Benzo[b]thiophene Dehydroamino Acids by Suzuki Palladium Catalyzed Cross Coupling

Abstract

α, β-Dehydroamino acids are an important class of non-proteinogenic compounds. Some of them are found in natural biologically active peptides, and, when inserted in peptide chains, cause conformational constraints [1]. In addition, they are valuable synthons for chemical synthesis of new amino acids [2]. Recently, we developed an efficient method for the dehydration of β-hydroxyamino acids to obtain C-protected N-acyl-N-Boc-dehydroamino acids [3], We now report the use of these compounds as precursors for palladium-catalyzed Suzuki cross-couplings [4] to give ß-benzo-[b]thiophene dehydroamino acids.