{"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":"metacan-v3-hybrid-931329e0061c","candidate_categories":[],"consensus_categories":[],"category_scores_codex":[0.0004405076,0.001245313,0.0003719591,0.0006019788,0.0003537354,0.0002586569,0.0007071446,0.0005605262,0.002777217],"category_scores_gemma":[0.0002472923,0.0003703253,0.0002122574,0.0002753634,0.0004464198,0.0007228064,0.00110355,0.001011131,0.00198733],"about_ca_system_candidate":false,"about_ca_system_consensus":false,"about_ca_system_score_codex":0.0003058419,"about_ca_system_score_gemma":0.0004677614,"about_ca_topic_candidate":false,"about_ca_topic_consensus":false,"about_ca_topic_score_codex":0.0003439711,"about_ca_topic_score_gemma":0.001132083,"domain_scores_codex":[0.9996942,0.00004322238,0.00002710569,0.00008312974,0.00008703086,0.00006535403],"domain_scores_gemma":[0.9998697,0.0000162541,0.00004115613,0.00002330297,0.00001820906,0.00003130408],"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":[0.0001328441,0.00008002407,0.0003534931,0.0003897647,0.00002699992,0.0004984706,0.0001020159,0.0002407542,0.966029,0.002696855,0.001242418,0.02820729],"study_design_scores_gemma":[0.00002026115,0.0003397786,0.0005183525,0.00001651436,0.00002482775,0.001227566,0.00001603587,0.0003158786,0.972967,0.0002336257,0.02429617,0.00002401042],"study_design_candidate":"bench_or_experimental","study_design_consensus":"bench_or_experimental","genre_codex":"empirical","genre_gemma":"empirical","genre_scores_codex":[0.5407898,0.02414682,0.3742936,0.0007984572,0.001082123,0.001250132,0.00267705,0.005340371,0.04962147],"genre_scores_gemma":[0.9088051,0.007037506,0.06894581,0.0003168134,0.0001888555,0.0003926762,0.001761211,0.0001753914,0.01237669],"genre_candidate":"empirical","genre_consensus":"empirical","teacher_disagreement_score":0.002777217,"threshold_uncertainty_score":0.009290695,"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."}}