posted on 2021-07-26, 18:03authored byTomer
M. Faraggi, Caroline Rouget-Virbel, Juan A. Rincón, Mario Barberis, Carlos Mateos, Susana García-Cerrada, Javier Agejas, Oscar de Frutos, David W. C. MacMillan
We describe herein a two-step process
for the conversion of serine
to a wide array of optically pure unnatural amino acids. This method
utilizes a photocatalytic cross-electrophile coupling between a bromoalkyl
intermediate and a diverse set of aryl halides to produce artificial
analogues of phenylalanine, tryptophan, and histidine. The reaction
is tolerant of a broad range of functionalities and can be leveraged
toward the scalable synthesis of valuable pharmaceutical scaffolds
via flow technology.