{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Zhou B"],"funding":["Division of Chemistry","European Research Council"],"pagination":["8361-8365"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC11459507"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["26(39)"],"pubmed_abstract":["A straightforward and general strategy for the catalytic asymmetric synthesis of β<sup>3</sup>-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, <i>tert</i>-butyloxycarbonyl; OMs, methylsulfonate) in the presence of the base piperidine provides N-Boc-protected β<sup>3</sup>-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<sup>3</sup>)-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"],"journal":["Organic letters"],"pubmed_title":["β&lt;sup&gt;3&lt;/sup&gt;-Tryptophans by Iron-Catalyzed Enantioselective Amination of 3-Indolepropionic Acids."],"pmcid":["PMC11459507"],"funding_grant_id":["CHE-2338438","883212"],"pubmed_authors":["Ivlev SI","Meggers E","Zhou B","Ih MI","Yao S","Hemming M","Chen S"],"additional_accession":[]},"is_claimable":false,"name":"β&lt;sup&gt;3&lt;/sup&gt;-Tryptophans by Iron-Catalyzed Enantioselective Amination of 3-Indolepropionic Acids.","description":"A straightforward and general strategy for the catalytic asymmetric synthesis of β<sup>3</sup>-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, <i>tert</i>-butyloxycarbonyl; OMs, methylsulfonate) in the presence of the base piperidine provides N-Boc-protected β<sup>3</sup>-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<sup>3</sup>)-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","dates":{"release":"2024-01-01T00:00:00Z","publication":"2024 Oct","modification":"2025-04-04T01:54:36.684Z","creation":"2025-04-04T01:54:36.684Z"},"accession":"S-EPMC11459507","cross_references":{"pubmed":["39311759"],"doi":["10.1021/acs.orglett.4c03130"]}}