{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Nguyen TH"],"funding":["Center for Selective C-H Functionalization, National Science Foundation","Lilly Research Award Program"],"pagination":["28098-28106"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC12333343"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["147(31)"],"pubmed_abstract":["Dirhodium tetracarboxylate-catalyzed reaction of aryldiazoacetates with <i>N</i>-Boc-2,5-dihydro-1<i>H</i>-pyrrole results in a highly enantio- and diastereoselective C-H functionalization exclusively at the α-<i>N</i> C2 position. This result is a sharp contrast to the reaction with ethyl diazoacetate, which results in cyclopropanation of the olefinic site. Rh<sub>2</sub>(<i>S</i>- or <i>R</i>-PTAD)<sub>4</sub> is the optimal chiral catalyst and is capable of generating the C-H functionalization products in up to 87% yield with high levels of diastereoselectivity (>20:1 d.r.) and enantioselectivity (97% ee) with a low catalyst loading (0.05 mol %). Computational studies were conducted to rationalize the reactivity difference between donor/acceptor carbenes and acceptor carbenes. The utili"],"journal":["Journal of the American Chemical Society"],"pubmed_title":["Asymmetric C-H Functionalization of &lt;i&gt;N&lt;/i&gt;-Boc-2,5-dihydro-1&lt;i&gt;H&lt;/i&gt;-pyrrole and Its Application as a Key Step in the Synthesis of (-)-Dragocin D."],"pmcid":["PMC12333343"],"funding_grant_id":["CHE-1700982"],"pubmed_authors":["Shimabukuro K","Davies HML","Nguyen TH","Bacsa J","Musaev DG","Navarro A"],"additional_accession":[]},"is_claimable":false,"name":"Asymmetric C-H Functionalization of &lt;i&gt;N&lt;/i&gt;-Boc-2,5-dihydro-1&lt;i&gt;H&lt;/i&gt;-pyrrole and Its Application as a Key Step in the Synthesis of (-)-Dragocin D.","description":"Dirhodium tetracarboxylate-catalyzed reaction of aryldiazoacetates with <i>N</i>-Boc-2,5-dihydro-1<i>H</i>-pyrrole results in a highly enantio- and diastereoselective C-H functionalization exclusively at the α-<i>N</i> C2 position. This result is a sharp contrast to the reaction with ethyl diazoacetate, which results in cyclopropanation of the olefinic site. Rh<sub>2</sub>(<i>S</i>- or <i>R</i>-PTAD)<sub>4</sub> is the optimal chiral catalyst and is capable of generating the C-H functionalization products in up to 87% yield with high levels of diastereoselectivity (>20:1 d.r.) and enantioselectivity (97% ee) with a low catalyst loading (0.05 mol %). Computational studies were conducted to rationalize the reactivity difference between donor/acceptor carbenes and acceptor carbenes. The utili","dates":{"release":"2025-01-01T00:00:00Z","publication":"2025 Aug","modification":"2026-04-15T19:11:15.521Z","creation":"2026-04-07T14:01:01.906Z"},"accession":"S-EPMC12333343","cross_references":{"pubmed":["40721903"],"doi":["10.1021/jacs.5c08080"]}}