Ethyl 2,2-bis(4-methylphenylsulfonamido)acetate to aromatic alpha-amino acids: stable substrates for catalytic arylation reactions

• Autor(a) principal: Burke, Anthony
• Data de Publicação: 2013
• Outros Autores: Marques, Carolina
• Tipo de documento: Artigo
• Idioma: por
• Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
• Texto Completo: http://hdl.handle.net/10174/9971; https://doi.org/10.1016/j.tet.2013.09.053
• topic: Síntese; Catálise

This paper reports the development of a novel methodology for the catalytic synthesis of aromatic alpha-amino acids, which involves the addition of aryl-organoboron reagents to alpha,alpha-ditosylamino esters derived from ethyl glyoxylate, using transition metal catalysts, like Rh and Pd. A library of alpha-amino esters (12 with Pd and 8 with Rh), was synthesized with moderate to excellent yields. A highest enantioselectivity of 30% ee was obtained using Hayashi's ligand. This method was applied to the synthesis of phenylglycine.