{"id":"https://openalex.org/W3003235602","doi":"https://doi.org/10.1039/c9ob02556a","title":"Elucidation of the atroposelectivity in the synthesis of axially chiral thiohydantoin derivatives","display_name":"Elucidation of the atroposelectivity in the synthesis of axially chiral thiohydantoin derivatives","publication_year":2020,"publication_date":"2020-01-01","ids":{"openalex":"https://openalex.org/W3003235602","doi":"https://doi.org/10.1039/c9ob02556a","mag":"3003235602","pmid":"https://pubmed.ncbi.nlm.nih.gov/32022073"},"language":"en","primary_location":{"id":"doi:10.1039/c9ob02556a","doi":"https://doi.org/10.1039/c9ob02556a","is_oa":false,"landing_page_url":"https://doi.org/10.1039/c9ob02556a","pdf_url":null,"source":{"id":"https://openalex.org/S179810352","display_name":"Organic & Biomolecular Chemistry","issn_l":"1477-0520","issn":["1477-0520","1477-0539"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-b","jufo-2","ki-jl-1","medline","norway-1","poland-100","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320556","host_organization_name":"Royal Society of Chemistry","host_organization_lineage":["https://openalex.org/P4310320556"],"host_organization_lineage_names":["Royal Society of Chemistry"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Organic & Biomolecular Chemistry","raw_type":"journal-article"},"volume":null,"type":"article","indexed_in":["crossref","pubmed"],"open_access":{"is_oa":false,"oa_status":"closed","oa_url":null,"any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5037400045","display_name":"Zeynep Pinar Haslak","orcid":"https://orcid.org/0000-0002-2850-9816","observed_orcids":["https://orcid.org/0000-0002-2850-9816"]},"institutions":[{"id":"https://openalex.org/I101840525","display_name":"Piri Reis University","ror":"https://ror.org/02eq60031","country_code":"TR","type":"education","lineage":["https://openalex.org/I101840525"]},{"id":"https://openalex.org/I4405392","display_name":"Bo\u011fazi\u00e7i University","ror":"https://ror.org/03z9tma90","country_code":"TR","type":"education","lineage":["https://openalex.org/I4405392"]},{"id":"https://openalex.org/I90183372","display_name":"Universit\u00e9 de Lorraine","ror":"https://ror.org/04vfs2w97","country_code":"FR","type":"education","lineage":["https://openalex.org/I90183372"]}],"countries":["FR","TR"],"is_corresponding":false,"raw_author_name":"Zeynep Pinar Haslak","raw_affiliation_strings":["Bogazi\u00e7i University","Department of Chemistry","Istanbul","Turkey","Universit\u00e9 de Lorraine","Faculty of Science and Letters, Piri Reis University, Tuzla, Istanbul, Turkey"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Bogazi\u00e7i University","institution_ids":["https://openalex.org/I4405392"]},{"raw_affiliation_string":"Department of Chemistry","institution_ids":[]},{"raw_affiliation_string":"Istanbul","institution_ids":[]},{"raw_affiliation_string":"Turkey","institution_ids":[]},{"raw_affiliation_string":"Universit\u00e9 de Lorraine","institution_ids":["https://openalex.org/I90183372"]},{"raw_affiliation_string":"Faculty of Science and Letters, Piri Reis University, Tuzla, Istanbul, Turkey","institution_ids":["https://openalex.org/I101840525"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5035658288","display_name":"Sesil Agopcan \u00c7\u0131nar","orcid":"https://orcid.org/0000-0002-4696-4003","observed_orcids":["https://orcid.org/0000-0002-4696-4003","https://orcid.org/0000-0002-6163-2074"]},"institutions":[{"id":"https://openalex.org/I4405392","display_name":"Bo\u011fazi\u00e7i University","ror":"https://ror.org/03z9tma90","country_code":"TR","type":"education","lineage":["https://openalex.org/I4405392"]}],"countries":["TR"],"is_corresponding":false,"raw_author_name":"Sesil Agopcan Cinar","raw_affiliation_strings":["Bogazi\u00e7i University","Department of Chemistry","Istanbul","Turkey"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Bogazi\u00e7i University","institution_ids":["https://openalex.org/I4405392"]},{"raw_affiliation_string":"Department of Chemistry","institution_ids":[]},{"raw_affiliation_string":"Istanbul","institution_ids":[]},{"raw_affiliation_string":"Turkey","institution_ids":[]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5071290760","display_name":"Sevgi Sar\u0131g\u00fcl \u00d6zbek","orcid":"https://orcid.org/0000-0002-0676-2415","observed_orcids":["https://orcid.org/0000-0002-0676-2415"]},"institutions":[{"id":"https://openalex.org/I322491407","display_name":"Ac\u0131badem University","ror":"https://ror.org/01rp2a061","country_code":"TR","type":"education","lineage":["https://openalex.org/I322491407"]}],"countries":["TR"],"is_corresponding":false,"raw_author_name":"Sevgi Sarigul Ozbek","raw_affiliation_strings":["Acibadem Mehmet Ali Aydinlar University","Faculty of Pharmacy","Istanbul","Turkey","Faculty of Pharmacy, Acibadem Mehmet Ali Aydinlar University, Atasehir, Istanbul, Turkey"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Acibadem Mehmet Ali Aydinlar University","institution_ids":["https://openalex.org/I322491407"]},{"raw_affiliation_string":"Faculty of Pharmacy","institution_ids":[]},{"raw_affiliation_string":"Istanbul","institution_ids":[]},{"raw_affiliation_string":"Turkey","institution_ids":[]},{"raw_affiliation_string":"Faculty of Pharmacy, Acibadem Mehmet Ali Aydinlar University, Atasehir, Istanbul, Turkey","institution_ids":["https://openalex.org/I322491407"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5073776196","display_name":"G\u00e9rald Monard","orcid":"https://orcid.org/0000-0002-3378-3481","observed_orcids":["https://orcid.org/0000-0002-3378-3481"]},"institutions":[{"id":"https://openalex.org/I1294671590","display_name":"Centre National de la Recherche Scientifique","ror":"https://ror.org/02feahw73","country_code":"FR","type":"government","lineage":["https://openalex.org/I1294671590"]},{"id":"https://openalex.org/I4387156043","display_name":"Laboratoire de Physique et Chimie Th\u00e9oriques","ror":"https://ror.org/02atkd403","country_code":"FR","type":"facility","lineage":["https://openalex.org/I1294671590","https://openalex.org/I4387156043","https://openalex.org/I90183372"]},{"id":"https://openalex.org/I90183372","display_name":"Universit\u00e9 de Lorraine","ror":"https://ror.org/04vfs2w97","country_code":"FR","type":"education","lineage":["https://openalex.org/I90183372"]}],"countries":["FR"],"is_corresponding":false,"raw_author_name":"G\u00e9rald Monard","raw_affiliation_strings":["CNRS","F-54000 Nancy","France","LPCT","Universit\u00e9 de Lorraine"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"CNRS","institution_ids":["https://openalex.org/I1294671590"]},{"raw_affiliation_string":"F-54000 Nancy","institution_ids":[]},{"raw_affiliation_string":"France","institution_ids":[]},{"raw_affiliation_string":"LPCT","institution_ids":["https://openalex.org/I4387156043"]},{"raw_affiliation_string":"Universit\u00e9 de Lorraine","institution_ids":["https://openalex.org/I90183372"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5066691319","display_name":"\u0130lknur Do\u011fan","orcid":"https://orcid.org/0000-0003-1920-8453","observed_orcids":["https://orcid.org/0000-0003-1920-8453"]},"institutions":[{"id":"https://openalex.org/I4405392","display_name":"Bo\u011fazi\u00e7i University","ror":"https://ror.org/03z9tma90","country_code":"TR","type":"education","lineage":["https://openalex.org/I4405392"]}],"countries":["TR"],"is_corresponding":true,"raw_author_name":"Ilknur Dogan","raw_affiliation_strings":["Bogazi\u00e7i University","Department of Chemistry","Istanbul","Turkey"],"raw_orcid":"https://orcid.org/0000-0003-3430-8268","affiliations":[{"raw_affiliation_string":"Bogazi\u00e7i University","institution_ids":["https://openalex.org/I4405392"]},{"raw_affiliation_string":"Department of Chemistry","institution_ids":[]},{"raw_affiliation_string":"Istanbul","institution_ids":[]},{"raw_affiliation_string":"Turkey","institution_ids":[]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5066360588","display_name":"Vi\u0307ktorya Avi\u0307yente","orcid":"https://orcid.org/0000-0001-9430-4096","observed_orcids":["https://orcid.org/0000-0001-9430-4096"]},"institutions":[{"id":"https://openalex.org/I4405392","display_name":"Bo\u011fazi\u00e7i University","ror":"https://ror.org/03z9tma90","country_code":"TR","type":"education","lineage":["https://openalex.org/I4405392"]}],"countries":["TR"],"is_corresponding":true,"raw_author_name":"Viktorya Aviyente","raw_affiliation_strings":["Bogazi\u00e7i University","Department of Chemistry","Istanbul","Turkey"],"raw_orcid":"https://orcid.org/0000-0001-9430-4096","affiliations":[{"raw_affiliation_string":"Bogazi\u00e7i University","institution_ids":["https://openalex.org/I4405392"]},{"raw_affiliation_string":"Department of Chemistry","institution_ids":[]},{"raw_affiliation_string":"Istanbul","institution_ids":[]},{"raw_affiliation_string":"Turkey","institution_ids":[]}]}],"institutions":[],"countries_distinct_count":2,"institutions_distinct_count":6,"corresponding_author_ids":["https://openalex.org/A5066360588","https://openalex.org/A5066691319"],"corresponding_institution_ids":["https://openalex.org/I4405392"],"apc_list":null,"apc_paid":null,"fwci":0.5824,"has_fulltext":false,"cited_by_count":9,"citation_normalized_percentile":{"value":0.53098888,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":88,"max":97},"biblio":{"volume":"18","issue":"12","first_page":"2233","last_page":"2241"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T13115","display_name":"Axial and Atropisomeric Chirality Synthesis","score":0.9984999895095825,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},"topics":[{"id":"https://openalex.org/T13115","display_name":"Axial and Atropisomeric Chirality Synthesis","score":0.9984999895095825,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T10911","display_name":"Chemical Synthesis and Analysis","score":9.999999747378752e-05,"subfield":{"id":"https://openalex.org/subfields/1312","display_name":"Molecular Biology"},"field":{"id":"https://openalex.org/fields/13","display_name":"Biochemistry, Genetics and Molecular Biology"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},{"id":"https://openalex.org/T12191","display_name":"Chemical Reaction Mechanisms","score":9.999999747378752e-05,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/atroposelectivity","display_name":"atroposelectivity","score":0.9599999785423279},{"id":"https://openalex.org/keywords/2-thiohydantoin","display_name":"2-thiohydantoin","score":0.9129999876022339},{"id":"https://openalex.org/keywords/racemization","display_name":"racemization","score":0.703000009059906},{"id":"https://openalex.org/keywords/epimerization","display_name":"epimerization","score":0.7419999837875366},{"id":"https://openalex.org/keywords/cyclization-mechanism","display_name":"cyclization mechanism","score":0.7059999704360962},{"id":"https://openalex.org/keywords/steric-effects","display_name":"steric effects","score":0.6679999828338623},{"id":"https://openalex.org/keywords/electrostatic-effects","display_name":"electrostatic effects","score":0.9929999709129333},{"id":"https://openalex.org/keywords/computational-chemistry","display_name":"computational chemistry","score":0.36899998784065247},{"id":"https://openalex.org/keywords/m06-2x","display_name":"M06-2X","score":0.9070000052452087}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.8997681140899658},{"id":"https://openalex.org/C60002323","wikidata":"https://www.wikidata.org/wiki/Q25819","display_name":"Racemization","level":2,"score":0.7459758520126343},{"id":"https://openalex.org/C201194858","wikidata":"https://www.wikidata.org/wiki/Q898238","display_name":"Steric effects","level":2,"score":0.618520975112915},{"id":"https://openalex.org/C35377427","wikidata":"https://www.wikidata.org/wiki/Q3886264","display_name":"Axial symmetry","level":2,"score":0.5896547436714172},{"id":"https://openalex.org/C131779359","wikidata":"https://www.wikidata.org/wiki/Q471875","display_name":"Amine gas treating","level":2,"score":0.5183849930763245},{"id":"https://openalex.org/C2780400988","wikidata":"https://www.wikidata.org/wiki/Q421748","display_name":"Dichloromethane","level":3,"score":0.5102863311767578},{"id":"https://openalex.org/C203130289","wikidata":"https://www.wikidata.org/wiki/Q926272","display_name":"Epimer","level":2,"score":0.4380631744861603},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.3676985502243042},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.34220027923583984},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.3042988181114197},{"id":"https://openalex.org/C2780471494","wikidata":"https://www.wikidata.org/wiki/Q146505","display_name":"Solvent","level":2,"score":0.1009669303894043},{"id":"https://openalex.org/C66938386","wikidata":"https://www.wikidata.org/wiki/Q633538","display_name":"Structural engineering","level":1,"score":0.0},{"id":"https://openalex.org/C127413603","wikidata":"https://www.wikidata.org/wiki/Q11023","display_name":"Engineering","level":0,"score":0.0}],"mesh":[],"locations_count":3,"locations":[{"id":"doi:10.1039/c9ob02556a","doi":"https://doi.org/10.1039/c9ob02556a","is_oa":false,"landing_page_url":"https://doi.org/10.1039/c9ob02556a","pdf_url":null,"source":{"id":"https://openalex.org/S179810352","display_name":"Organic & Biomolecular Chemistry","issn_l":"1477-0520","issn":["1477-0520","1477-0539"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-b","jufo-2","ki-jl-1","medline","norway-1","poland-100","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320556","host_organization_name":"Royal Society of Chemistry","host_organization_lineage":["https://openalex.org/P4310320556"],"host_organization_lineage_names":["Royal Society of Chemistry"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Organic & Biomolecular Chemistry","raw_type":"journal-article"},{"id":"pmid:32022073","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/32022073","pdf_url":null,"source":{"id":"https://openalex.org/S4306525036","display_name":"PubMed","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1299303238","host_organization_name":"National Institutes of Health","host_organization_lineage":["https://openalex.org/I1299303238"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Organic & biomolecular chemistry","raw_type":"Journal Article"},{"id":"pmh:oai:HAL:hal-03259112v1","doi":null,"is_oa":false,"landing_page_url":"https://hal.univ-lorraine.fr/hal-03259112","pdf_url":null,"source":{"id":"https://openalex.org/S4306402512","display_name":"HAL","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I4405252976","host_organization_name":"Centre pour la Communication Scientifique Directe","host_organization_lineage":["https://openalex.org/I4405252976"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":"Organic & Biomolecular Chemistry, 2020, 18, pp.2233 - 2241. ⟨10.1039/c9ob02556a⟩","raw_type":"info:eu-repo/semantics/article"}],"best_oa_location":null,"sustainable_development_goals":[],"sustainable_development_goals_aurora":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G4987786554","display_name":null,"funder_award_id":"16241","funder_id":"https://openalex.org/F4320323079","funder_display_name":"Bo\u011fazi\u00e7i \u00dcniversitesi"}],"funders":[{"id":"https://openalex.org/F4320323079","display_name":"Bo\u011fazi\u00e7i \u00dcniversitesi","ror":"https://ror.org/03z9tma90"}],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":46,"referenced_works":["https://openalex.org/W1964417474","https://openalex.org/W1964684995","https://openalex.org/W1964775984","https://openalex.org/W1978061428","https://openalex.org/W1992173555","https://openalex.org/W2009527924","https://openalex.org/W2012902780","https://openalex.org/W2015070681","https://openalex.org/W2015635525","https://openalex.org/W2022978037","https://openalex.org/W2023810497","https://openalex.org/W2034623153","https://openalex.org/W2038083805","https://openalex.org/W2039998738","https://openalex.org/W2065159780","https://openalex.org/W2069317559","https://openalex.org/W2080073381","https://openalex.org/W2084015970","https://openalex.org/W2084568881","https://openalex.org/W2085336624","https://openalex.org/W2100055306","https://openalex.org/W2104426111","https://openalex.org/W2120901082","https://openalex.org/W2121765510","https://openalex.org/W2127336290","https://openalex.org/W2142331491","https://openalex.org/W2150697053","https://openalex.org/W2168978541","https://openalex.org/W2171650541","https://openalex.org/W2298078127","https://openalex.org/W2313238185","https://openalex.org/W2317130155","https://openalex.org/W2319256513","https://openalex.org/W2320067030","https://openalex.org/W2324735414","https://openalex.org/W2472035836","https://openalex.org/W2611267954","https://openalex.org/W2754480017","https://openalex.org/W2766437429","https://openalex.org/W2767110768","https://openalex.org/W2791967961","https://openalex.org/W2950014944","https://openalex.org/W2950575221","https://openalex.org/W2951349992","https://openalex.org/W4240818255","https://openalex.org/W4243079614"],"related_works":["https://openalex.org/W2472035836","https://openalex.org/W4281639783","https://openalex.org/W4406771024","https://openalex.org/W1955075753","https://openalex.org/W3205945521","https://openalex.org/W2058378621","https://openalex.org/W4220777793","https://openalex.org/W2052587536","https://openalex.org/W2952089172","https://openalex.org/W1999866884"],"abstract_inverted_index":{"Recently,":[0],"Sarigul":[1],"and":[2,23,74,88],"Dogan":[3],"have":[4],"synthesized":[5],"a":[6,41,65],"number":[7],"of":[8,18,29,56],"enantiomerically":[9],"enriched":[10],"axially":[11,46],"chiral":[12,37,47],"atropoisomeric":[13],"2-thiohydantoins":[14],"by":[15],"the":[16,27,45,57,86,104,109],"reaction":[17],"l-amino":[19],"acid":[20],"ester":[21],"salts":[22],"o-aryl":[24],"isothiocyanates":[25],"in":[26,33,79],"presence":[28],"triethyl":[30],"amine":[31],"(TEA)":[32],"dichloromethane.":[34],"The":[35,94],"non-axially":[36],"derivative":[38],"5-methyl-3-phenyl-2-thiohydantoin":[39],"gave":[40],"racemic":[42],"product":[43],"whereas":[44],"5-methyl-3-o-bromophenyl-2-thiohydantoin":[48],"was":[49],"less":[50],"prone":[51],"to":[52,81,107],"racemize":[53],"at":[54,112],"C5":[55],"heterocyclic":[58],"ring.":[59],"In":[60],"this":[61],"study,":[62],"we":[63],"present":[64],"computational":[66],"study":[67,95],"(M06-2X/6-311+G(d,p)":[68],"for":[69,77,85,91],"C,":[70],"H,":[71],"O,":[72],"N":[73],"S;":[75],"M06-2X/6-311++G(3df,3pd)":[76],"Br)":[78],"order":[80],"propose":[82],"plausible":[83],"mechanisms":[84],"racemization":[87],"cyclization":[89],"steps":[90],"2-thiohydantoin":[92],"derivatives.":[93],"includes":[96],"rationalization":[97],"based":[98],"on":[99],"steric":[100],"as":[101,103],"well":[102],"electrostatic":[105],"effects":[106],"elucidate":[108],"epimerization":[110],"differences":[111],"C5.":[113]},"counts_by_year":[{"year":2025,"cited_by_count":1},{"year":2024,"cited_by_count":2},{"year":2023,"cited_by_count":1},{"year":2022,"cited_by_count":4},{"year":2021,"cited_by_count":1}],"updated_date":"2026-10-25T09:29:13.331239","created_date":"2020-02-07T00:00:00"}