Year: 2024
Type: article
Abstract: High Resolution Image Download MS PowerPoint Slide A straightforward and general strategy for the catalytic asymmetric synthesis of β 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 β 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.
Source: Organic Letters
Institutions: Philipps University of Marburg, Oberlin College
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $4,500
OpenAlex ID: W4402732300