{"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":"metacan-v3-hybrid-931329e0061c","candidate_categories":[],"consensus_categories":[],"category_scores_codex":[0.0001355607,0.0005235401,0.0001508373,0.0002136177,0.0001597336,0.000159027,0.0003417128,0.0002016697,0.001725307],"category_scores_gemma":[0.0001079673,0.0002156422,0.0002033734,0.0001397856,0.0001728243,0.0004067349,0.0002529134,0.000530573,0.0006787152],"about_ca_system_candidate":false,"about_ca_system_consensus":false,"about_ca_system_score_codex":0.0002069676,"about_ca_system_score_gemma":0.000359418,"about_ca_topic_candidate":false,"about_ca_topic_consensus":false,"about_ca_topic_score_codex":0.0004687754,"about_ca_topic_score_gemma":0.001102327,"domain_scores_codex":[0.9999295,0.00000903544,0.000009013175,0.00001968077,0.00001558035,0.00001701679],"domain_scores_gemma":[0.9999436,0.000005197193,0.00001915431,0.000009152238,0.000009192959,0.00001364366],"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":[0.00006847033,0.00003115255,0.0001232324,0.000182919,0.00001220706,0.00024566,0.00007658746,0.0001581646,0.9876444,0.001743202,0.0002959029,0.009418016],"study_design_scores_gemma":[0.0000508675,0.0007675751,0.001063235,0.00001890599,0.00003175787,0.00122386,0.00003954114,0.0007707322,0.9652184,0.0003209377,0.03046899,0.00002511876],"study_design_candidate":"bench_or_experimental","study_design_consensus":"bench_or_experimental","genre_codex":"empirical","genre_gemma":"empirical","genre_scores_codex":[0.8600309,0.01212286,0.08975861,0.0006152697,0.0003461046,0.0004400262,0.001411596,0.001413747,0.03386081],"genre_scores_gemma":[0.9602116,0.00449616,0.02745459,0.0001310782,0.00003922604,0.0001511165,0.0007032608,0.00007295573,0.00673994],"genre_candidate":"empirical","genre_consensus":"empirical","teacher_disagreement_score":0.001725307,"threshold_uncertainty_score":0.005771756,"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."}}