189700-13-8Relevant academic research and scientific papers
N–H insertion reaction via an iron carbenoid from α-diazophenylpropionate and its application to the formal total synthesis of stizolobinic acid
Homma, Hiroki,Miyairi, Shinichi,Mizuta, Katsumi,Saito, Hiroaki,Shinohara, Hideyuki,Uchiyama, Taketo
, (2020/10/13)
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.
A biomimetic synthesis of stizolobinic acid
Baldwin, Jack E.,Spyvee, Mark R.,Whitehead, Roger C.
, p. 2771 - 2774 (2007/10/03)
Stizolobinic acid (1) was synthesized in a biomimetic fashion from an analogue of L-DOPA via an oxidative cleavage reaction.
