Enantioselective Synthesis of Chiral Amines via Biocatalytic Carbene N-H Insertion.

ABSTRACT: Optically active amines represent highly valuable building blocks for the synthesis of advanced pharmaceutical intermediates, drug molecules, and biologically active natural products. Hemoproteins have recently emerged as promising biocatalysts for the formation of C-N bonds via carbene transfer, but asymmetric N-H carbene insertion reactions using these or other enzymes have so far been elusive. Here, we report the successful development of a biocatalytic strategy for the asymmetric N-H carbene insertion of aromatic amines with 2-diazopropanoate esters using engineered variants of myoglobin. High activity and stereoinduction in this reaction could be achieved by tuning the chiral environment around the heme cofactor in the metalloprotein in combination with catalyst-matching and tailoring

SUBMITTER: Steck V 

PROVIDER: S-EPMC8412361 | biostudies-literature | 2020 Oct

REPOSITORIES: biostudies-literature