{"id":"W2220073116","doi":"10.1021/jacs.5b11288","title":"Synthesis of Enantiopure Piperazines via Asymmetric Lithiation–Trapping of <i>N</i>-Boc Piperazines: Unexpected Role of the Electrophile and Distal <i>N</i>-Substituent","year":2015,"lang":"en","type":"article","venue":"Journal of the American Chemical Society","topic":"Coordination Chemistry and Organometallics","field":"Chemistry","cited_by":59,"is_retracted":false,"has_abstract":true,"ca_institutions":"","funders":"Engineering and Physical Sciences Research Council; York University; AstraZeneca","keywords":"Enantiopure drug; Chemistry; Substituent; Electrophile; Piperazine; Combinatorial chemistry; Enantioselective synthesis; Stereochemistry; Organic chemistry; Catalysis","routes":{"ca_aff":false,"ca_fund":true,"ca_venue":false,"about_ca":false,"invisible_to_affiliation_only":true},"retraction":null,"screen":null,"direct_labels":[],"prediction":{"model_version":"codex-gemma-dda1882f352a","candidate_categories":[],"consensus_categories":[],"category_scores_codex":[0.0002718221,0.0001907237,0.0005853928,0.00002981513,0.00006585014,0.00001316538,0.0005731466,0.00009452929,0.00002214267],"category_scores_gemma":[0.0009043067,0.000118085,0.0006009277,0.001122168,0.0006216267,0.00009214129,0.0001625235,0.0003663643,1.708847e-7],"about_ca_system_candidate":false,"about_ca_system_consensus":false,"about_ca_system_score_codex":0.0001239598,"about_ca_system_score_gemma":0.0001859716,"about_ca_topic_candidate":false,"about_ca_topic_consensus":false,"about_ca_topic_score_codex":0.00003349057,"about_ca_topic_score_gemma":8.026907e-7,"domain_scores_codex":[0.9981982,0.00004376548,0.0007897783,0.0001594072,0.0006192738,0.0001895757],"domain_scores_gemma":[0.9967972,0.0003159768,0.001875539,0.0003245066,0.0005772087,0.0001095824],"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":[0.0000698182,0.0002091011,0.01214438,0.0001328211,0.0002179391,2.306822e-7,0.0004451926,0.00003190521,0.984705,0.00001490944,0.0004244681,0.001604246],"study_design_scores_gemma":[0.0004126286,0.00002604124,0.002121879,0.0001196447,0.000198932,0.00004288767,0.001182295,0.0002259392,0.9946361,0.0001849239,0.0007239857,0.0001247854],"study_design_candidate":"bench_or_experimental","study_design_consensus":"bench_or_experimental","genre_codex":"empirical","genre_gemma":"empirical","genre_scores_codex":[0.9977828,0.000866383,0.0001099342,0.0007199524,0.00004540762,0.00004809499,0.00002859357,0.00001047547,0.0003883084],"genre_scores_gemma":[0.9989796,0.0001884341,0.00055316,0.00005374665,0.0001577804,0.00000281584,0.000001666107,0.00002118205,0.00004160595],"genre_candidate":"empirical","genre_consensus":"empirical","teacher_disagreement_score":0.0100225,"threshold_uncertainty_score":0.4815365,"prediction_status":"machine_predicted_unvalidated"},"machine_scores":{"provisional":true,"baseline":true,"maturity_gate_passed":false,"score_opus":0.006232778637313526,"score_gpt":0.2108910311664269,"score_spread":0.2046582525291134,"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."}}