β³-Tryptophans by Iron-Catalyzed Enantioselective Amination of 3-Indolepropionic Acids.

ABSTRACT: A straightforward and general strategy for the catalytic asymmetric synthesis of β³-tryptophans by carboxylic-acid-directed intermolecular C-H amination has been developed. The iron-catalyzed C-H amination of 3-indolepropionic acids with BocNHOMs (Boc, tert-butyloxycarbonyl; OMs, methylsulfonate) in the presence of the base piperidine provides N-Boc-protected β³-tryptophans in a single step with high enantiomeric excess (ee) of up to >99%. Mechanistic experiments and density functional theory calculations support a mechanism through carboxylate-directed iron-mediated C(sp³)-H nitrene insertion. The method incorporates two key sustainability criteria: the use of iron as an abundant, non-toxic, and environmentally benign metal, along with the achieveme

SUBMITTER: Zhou B 

PROVIDER: S-EPMC11459507 | biostudies-literature | 2024 Oct

REPOSITORIES: biostudies-literature