{"id":"W2950344408","doi":"10.1021/jo000080p","title":"A Convenient New Route to Piperidines, Pyrrolizidines, Indolizidines, and Quinolizidines by Cyclization of Acetylenic Sulfones with β- and γ-Chloroamines. Enantioselective Total Synthesis of Indolizidines<b>(</b><b>−</b><b>)-167B</b>,<b>(</b><b>−</b><b>)-209D</b>,<b>(</b><b>−</b><b>)-209B</b>, and<b>(</b><b>−</b><b>)-207A</b>","year":2000,"lang":"en","type":"article","venue":"The Journal of Organic Chemistry","topic":"Sulfur-Based Synthesis Techniques","field":"Chemistry","cited_by":84,"is_retracted":false,"has_abstract":true,"ca_institutions":"University of Calgary","funders":"Natural Sciences and Engineering Research Council of Canada","keywords":"Chemistry; Indolizidine; Enantioselective synthesis; Carbanion; Enamine; Stereochemistry; Acylation; Enantiopure drug; Sodium cyanoborohydride; Alkylation; Hydrocyanation; Intramolecular force; Medicinal chemistry; Organic chemistry; 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":["metaepi_narrow","insufficient_payload"],"consensus_categories":["metaepi_narrow"],"category_scores_codex":[0.001897707,0.001948639,0.003313397,0.0006318656,0.0004717997,0.000195229,0.00169347,0.0009707049,0.001505427],"category_scores_gemma":[0.001803611,0.001508603,0.0004439686,0.001952505,0.001763744,0.001039066,0.0006487037,0.001301304,0.000008122926],"about_ca_system_candidate":false,"about_ca_system_consensus":false,"about_ca_system_score_codex":0.0003655541,"about_ca_system_score_gemma":0.001045336,"about_ca_topic_candidate":false,"about_ca_topic_consensus":false,"about_ca_topic_score_codex":0.0006593658,"about_ca_topic_score_gemma":0.00009349324,"domain_scores_codex":[0.9910057,0.000351886,0.003647233,0.001491587,0.001943473,0.001560074],"domain_scores_gemma":[0.9907249,0.002133563,0.002725525,0.001759748,0.001320565,0.001335651],"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":[0.003935867,0.0005984124,0.009717911,0.001430491,0.0007013764,0.00003158086,0.002059476,0.00004530323,0.9630307,0.00007856693,0.001870113,0.01650022],"study_design_scores_gemma":[0.004192423,0.0007730825,0.002709538,0.00198533,0.001552599,0.003063901,0.001825149,0.0001263264,0.9792705,0.0003494967,0.002522888,0.001628823],"study_design_candidate":"bench_or_experimental","study_design_consensus":"bench_or_experimental","genre_codex":"empirical","genre_gemma":"empirical","genre_scores_codex":[0.986176,0.008812306,0.0007380993,0.001746809,0.0001220866,0.0008112687,0.0003217366,0.0002791352,0.0009926123],"genre_scores_gemma":[0.9867402,0.009000016,0.001789771,0.0001972403,0.0005852538,0.00007403993,0.00004308462,0.0004550473,0.001115369],"genre_candidate":"empirical","genre_consensus":"empirical","teacher_disagreement_score":0.01623976,"threshold_uncertainty_score":0.9994074,"prediction_status":"machine_predicted_unvalidated"},"machine_scores":{"provisional":true,"baseline":true,"maturity_gate_passed":false,"score_opus":0.004460806752540516,"score_gpt":0.1957822677229421,"score_spread":0.1913214609704016,"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."}}