N–H insertion reaction via an iron carbenoid from α-diazophenylpropionate and its application to the formal total synthesis of stizolobinic acid

Article abstract of DOI:10.1016/j.tet.2020.131619

The formal total synthesis of the non-proteinogenic amino acid stizolobinic acid was accomplished relying as key step on an iron carbenoid-based N–H insertion reaction. The N–H insertion of α-diazophenylpropionate and benzylamine derivative catalyzed by tetrakis(pentafluorophenyl)porphyrin iron (III) chloride afforded the desired N–H insertion product in 79% yield. This is the first example of an N–H insertion involving α-diazophenylpropionate and an aliphatic amine catalyzed by an iron(III) porphyrin complex.