{"id":"W4407295740","doi":"10.1002/anie.202420312","title":"Universal Reagent for Mild and Stereospecific Nucleophilic Substitution of Alcohols with Amines","year":2025,"lang":"en","type":"article","venue":"Angewandte Chemie International Edition","topic":"Asymmetric Hydrogenation and Catalysis","field":"Chemistry","cited_by":13,"is_retracted":false,"has_abstract":true,"ca_institutions":"Université de Montréal; Centre in Green Chemistry and Catalysis","funders":"Fonds de recherche du Québec – Nature et technologies; Natural Sciences and Engineering Research Council of Canada; Université de Montréal; Agence Nationale de la Recherche; Centre in Green Chemistry and Catalysis","keywords":"Chemistry; Reagent; Nucleophile; Intramolecular force; Nucleophilic substitution; Protonation; Combinatorial chemistry; Amination; SN2 reaction; Nucleophilic aromatic substitution; Organic chemistry; Methanol; Mitsunobu reaction; Betaine; Iminium; Medicinal chemistry; Ion; Catalysis","routes":{"ca_aff":true,"ca_fund":true,"ca_venue":false,"about_ca":false,"invisible_to_affiliation_only":false},"retraction":null,"screen":null,"direct_labels":[],"prediction":{"model_version":"codex-gemma-dda1882f352a","candidate_categories":[],"consensus_categories":[],"category_scores_codex":[0.00005834119,0.00009680532,0.0001191608,0.0001604483,0.00005164813,0.00002230889,0.0001100693,0.00006978319,0.0002125902],"category_scores_gemma":[0.00005874799,0.00009074786,0.00005741554,0.0001819946,0.00008239842,0.0001557715,0.0000260198,0.00005060967,0.000001611869],"about_ca_system_candidate":false,"about_ca_system_consensus":false,"about_ca_system_score_codex":0.0001036986,"about_ca_system_score_gemma":0.00002584444,"about_ca_topic_candidate":false,"about_ca_topic_consensus":false,"about_ca_topic_score_codex":0.00001901258,"about_ca_topic_score_gemma":0.000009359849,"domain_scores_codex":[0.9993304,0.000002830191,0.0001877464,0.0002023169,0.000194197,0.00008251842],"domain_scores_gemma":[0.9994055,0.00007339363,0.0001223517,0.0001118768,0.0002552518,0.0000316001],"domain_codex":null,"domain_gemma":null,"domain_candidate":null,"domain_consensus":null,"study_design_codex":"bench_or_experimental","study_design_gemma":"bench_or_experimental","study_design_scores_codex":[0.00117633,0.0006163378,0.01054144,0.0006451764,0.001462443,0.0000111584,0.0005468127,0.00008756813,0.9004973,0.04684395,0.02075978,0.01681177],"study_design_scores_gemma":[0.001105571,0.00001566518,0.0008475372,0.00009068523,0.00007418956,0.000003360361,0.0002312518,0.0002237104,0.9692127,0.0004034174,0.02769935,0.00009253322],"study_design_candidate":"bench_or_experimental","study_design_consensus":"bench_or_experimental","genre_codex":"empirical","genre_gemma":"empirical","genre_scores_codex":[0.9083968,0.0003328494,0.02360291,0.001547309,0.0004972556,0.0002215658,0.0004976742,0.00009191903,0.06481171],"genre_scores_gemma":[0.9960293,0.0001118108,0.0002804924,0.00006550322,0.0002227093,0.00003003191,0.000888285,0.000007228299,0.002364613],"genre_candidate":"empirical","genre_consensus":"empirical","teacher_disagreement_score":0.08763251,"threshold_uncertainty_score":0.370059,"prediction_status":"machine_predicted_unvalidated"},"machine_scores":{"provisional":true,"baseline":true,"maturity_gate_passed":false,"score_opus":0.01456274974959761,"score_gpt":0.2529251394692756,"score_spread":0.238362389719678,"validation_status":"score_only:v0-immature-baseline","note":"Baseline scores from an immature model (maturity gate not passed). Scores rank; they never assert a category."}}