β3-Tryptophans by Iron-Catalyzed Enantioselective Amination of 3-Indolepropionic Acids
Abstract
A straightforward and general strategy for the catalytic asymmetric synthesis of beta(3)-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 beta(3)-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(sp(3))-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 achievement of streamlined enantioselective C-H functionalization.
Repository Citation
Zhou, Bing, Marisa I. Ih, Suyang Yao, et al. 2024. "β3-Tryptophans by Iron-Catalyzed Enantioselective Amination of 3-Indolepropionic Acids." Organic Letters 26(39): 8361-8365.
Publisher
American Chemical Society
Publication Date
10-4-2024
Publication Title
Organic Letters
Department
Chemistry and Biochemistry
Document Type
Article
DOI
https://doi.org/10.1021/acs.orglett.4c03130
Notes
Section: Letter
Keywords
Organic-synthesis, Beta-peptides, Metal, Functionalization, Chemistry
Language
English
Format
text
