{"id":"https://openalex.org/W4398197871","doi":"https://doi.org/10.1021/acs.oprd.4c00095","title":"Development of Asymmetric Reductive Amination of Unfunctionalized Ketone with Primary Amine","display_name":"Development of Asymmetric Reductive Amination of Unfunctionalized Ketone with Primary Amine","publication_year":2024,"publication_date":"2024-05-22","ids":{"openalex":"https://openalex.org/W4398197871","doi":"https://doi.org/10.1021/acs.oprd.4c00095"},"language":"en","primary_location":{"id":"doi:10.1021/acs.oprd.4c00095","doi":"https://doi.org/10.1021/acs.oprd.4c00095","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.oprd.4c00095","pdf_url":null,"source":{"id":"https://openalex.org/S107255770","display_name":"Organic Process Research & Development","issn_l":"1083-6160","issn":["1083-6160","1520-586X"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-b","jufo-1","norway-1","poland-100","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Organic Process Research &amp; Development","raw_type":"journal-article"},"volume":null,"type":"article","is_traditional":true,"indexed_in":["crossref"],"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/A5039471438","display_name":"Xiangyu Liu","orcid":"https://orcid.org/0000-0001-7442-228X","observed_orcids":["https://orcid.org/0000-0001-7442-228X"]},"institutions":[{"id":"https://openalex.org/I4210147685","display_name":"Jiangsu Hengrui Medicine (China)","ror":"https://ror.org/04ayvvz32","country_code":"CN","type":"company","lineage":["https://openalex.org/I4210147685"]}],"countries":["CN"],"is_corresponding":false,"raw_author_name":"Xiangyu Liu","raw_affiliation_strings":["Department of Chemical Process R&D, Lianyungang Institute of Research, Jiangsu Hengrui Pharmaceuticals Co., Ltd., 7 Kunlunshan Road, Lianyungang 222000, China"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemical Process R&D, Lianyungang Institute of Research, Jiangsu Hengrui Pharmaceuticals Co., Ltd., 7 Kunlunshan Road, Lianyungang 222000, China","institution_ids":["https://openalex.org/I4210147685"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5004434596","display_name":"Ensheng Zhan","orcid":"https://orcid.org/0000-0001-8560-2809","observed_orcids":["https://orcid.org/0000-0001-8560-2809"]},"institutions":[{"id":"https://openalex.org/I4210147685","display_name":"Jiangsu Hengrui Medicine (China)","ror":"https://ror.org/04ayvvz32","country_code":"CN","type":"company","lineage":["https://openalex.org/I4210147685"]}],"countries":["CN"],"is_corresponding":false,"raw_author_name":"Ensheng Zhan","raw_affiliation_strings":["Department of Chemical Process R&D, Lianyungang Institute of Research, Jiangsu Hengrui Pharmaceuticals Co., Ltd., 7 Kunlunshan Road, Lianyungang 222000, China"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemical Process R&D, Lianyungang Institute of Research, Jiangsu Hengrui Pharmaceuticals Co., Ltd., 7 Kunlunshan Road, Lianyungang 222000, China","institution_ids":["https://openalex.org/I4210147685"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5100656525","display_name":"Zhi Wang","orcid":"https://orcid.org/0000-0001-7851-4843","observed_orcids":["https://orcid.org/0000-0001-7851-4843"]},"institutions":[{"id":"https://openalex.org/I4210147685","display_name":"Jiangsu Hengrui Medicine (China)","ror":"https://ror.org/04ayvvz32","country_code":"CN","type":"company","lineage":["https://openalex.org/I4210147685"]}],"countries":["CN"],"is_corresponding":false,"raw_author_name":"Zhi Wang","raw_affiliation_strings":["Department of Chemical Process R&D, Lianyungang Institute of Research, Jiangsu Hengrui Pharmaceuticals Co., Ltd., 7 Kunlunshan Road, Lianyungang 222000, China"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemical Process R&D, Lianyungang Institute of Research, Jiangsu Hengrui Pharmaceuticals Co., Ltd., 7 Kunlunshan Road, Lianyungang 222000, China","institution_ids":["https://openalex.org/I4210147685"]}]},{"author_position":"middle","author":{"id":null,"display_name":"Guoliang Dong","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I4210147685","display_name":"Jiangsu Hengrui Medicine (China)","ror":"https://ror.org/04ayvvz32","country_code":"CN","type":"company","lineage":["https://openalex.org/I4210147685"]}],"countries":["CN"],"is_corresponding":false,"raw_author_name":"Guoliang Dong","raw_affiliation_strings":["Department of Chemical Process R&D, Lianyungang Institute of Research, Jiangsu Hengrui Pharmaceuticals Co., Ltd., 7 Kunlunshan Road, Lianyungang 222000, China"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemical Process R&D, Lianyungang Institute of Research, Jiangsu Hengrui Pharmaceuticals Co., Ltd., 7 Kunlunshan Road, Lianyungang 222000, China","institution_ids":["https://openalex.org/I4210147685"]}]},{"author_position":"middle","author":{"id":null,"display_name":"Gaochao Dong","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I4210147685","display_name":"Jiangsu Hengrui Medicine (China)","ror":"https://ror.org/04ayvvz32","country_code":"CN","type":"company","lineage":["https://openalex.org/I4210147685"]}],"countries":["CN"],"is_corresponding":false,"raw_author_name":"Gaochao Dong","raw_affiliation_strings":["Department of Chemical Process R&D, Lianyungang Institute of Research, Jiangsu Hengrui Pharmaceuticals Co., Ltd., 7 Kunlunshan Road, Lianyungang 222000, China"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemical Process R&D, Lianyungang Institute of Research, Jiangsu Hengrui Pharmaceuticals Co., Ltd., 7 Kunlunshan Road, Lianyungang 222000, China","institution_ids":["https://openalex.org/I4210147685"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5100669477","display_name":"Shuai Wu","orcid":"https://orcid.org/0000-0002-3183-5081","observed_orcids":["https://orcid.org/0000-0002-3183-5081"]},"institutions":[{"id":"https://openalex.org/I4210147685","display_name":"Jiangsu Hengrui Medicine (China)","ror":"https://ror.org/04ayvvz32","country_code":"CN","type":"company","lineage":["https://openalex.org/I4210147685"]}],"countries":["CN"],"is_corresponding":false,"raw_author_name":"Shuai Wu","raw_affiliation_strings":["Department of Chemical Process R&D, Lianyungang Institute of Research, Jiangsu Hengrui Pharmaceuticals Co., Ltd., 7 Kunlunshan Road, Lianyungang 222000, China"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemical Process R&D, Lianyungang Institute of Research, Jiangsu Hengrui Pharmaceuticals Co., Ltd., 7 Kunlunshan Road, Lianyungang 222000, China","institution_ids":["https://openalex.org/I4210147685"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5081716971","display_name":"Yunlin Zhang","orcid":"https://orcid.org/0000-0002-3382-4570","observed_orcids":["https://orcid.org/0000-0002-3382-4570"]},"institutions":[{"id":"https://openalex.org/I4210147685","display_name":"Jiangsu Hengrui Medicine (China)","ror":"https://ror.org/04ayvvz32","country_code":"CN","type":"company","lineage":["https://openalex.org/I4210147685"]}],"countries":["CN"],"is_corresponding":false,"raw_author_name":"Yunlin Zhang","raw_affiliation_strings":["Department of Chemical Process R&D, Lianyungang Institute of Research, Jiangsu Hengrui Pharmaceuticals Co., Ltd., 7 Kunlunshan Road, Lianyungang 222000, China"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemical Process R&D, Lianyungang Institute of Research, Jiangsu Hengrui Pharmaceuticals Co., Ltd., 7 Kunlunshan Road, Lianyungang 222000, China","institution_ids":["https://openalex.org/I4210147685"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5023912890","display_name":"Jingrui Chen","orcid":"https://orcid.org/0000-0001-5301-1465","observed_orcids":["https://orcid.org/0000-0001-5301-1465"]},"institutions":[{"id":"https://openalex.org/I4210147685","display_name":"Jiangsu Hengrui Medicine (China)","ror":"https://ror.org/04ayvvz32","country_code":"CN","type":"company","lineage":["https://openalex.org/I4210147685"]}],"countries":["CN"],"is_corresponding":false,"raw_author_name":"Jingrui Chen","raw_affiliation_strings":["Department of Chemical Process R&D, Lianyungang Institute of Research, Jiangsu Hengrui Pharmaceuticals Co., Ltd., 7 Kunlunshan Road, Lianyungang 222000, China"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemical Process R&D, Lianyungang Institute of Research, Jiangsu Hengrui Pharmaceuticals Co., Ltd., 7 Kunlunshan Road, Lianyungang 222000, China","institution_ids":["https://openalex.org/I4210147685"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5070019572","display_name":"Jialin Wen","orcid":"https://orcid.org/0000-0003-3328-3265","observed_orcids":["https://orcid.org/0000-0003-3328-3265"]},"institutions":[{"id":"https://openalex.org/I4210147685","display_name":"Jiangsu Hengrui Medicine (China)","ror":"https://ror.org/04ayvvz32","country_code":"CN","type":"company","lineage":["https://openalex.org/I4210147685"]}],"countries":["CN"],"is_corresponding":true,"raw_author_name":"Jialin Wen","raw_affiliation_strings":["Department of Chemical Process R&D, Lianyungang Institute of Research, Jiangsu Hengrui Pharmaceuticals Co., Ltd., 7 Kunlunshan Road, Lianyungang 222000, China"],"raw_orcid":"https://orcid.org/0000-0003-3328-3265","affiliations":[{"raw_affiliation_string":"Department of Chemical Process R&D, Lianyungang Institute of Research, Jiangsu Hengrui Pharmaceuticals Co., Ltd., 7 Kunlunshan Road, Lianyungang 222000, China","institution_ids":["https://openalex.org/I4210147685"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5071284490","display_name":"Lei Zhang","orcid":"https://orcid.org/0000-0002-0837-730X","observed_orcids":["https://orcid.org/0000-0002-0837-730X","https://orcid.org/0000-0002-6833-2488"]},"institutions":[{"id":"https://openalex.org/I4210147685","display_name":"Jiangsu Hengrui Medicine (China)","ror":"https://ror.org/04ayvvz32","country_code":"CN","type":"company","lineage":["https://openalex.org/I4210147685"]}],"countries":["CN"],"is_corresponding":false,"raw_author_name":"Lei Zhang","raw_affiliation_strings":["Department of Chemical Process R&D, Lianyungang Institute of Research, Jiangsu Hengrui Pharmaceuticals Co., Ltd., 7 Kunlunshan Road, Lianyungang 222000, China"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemical Process R&D, Lianyungang Institute of Research, Jiangsu Hengrui Pharmaceuticals Co., Ltd., 7 Kunlunshan Road, Lianyungang 222000, China","institution_ids":["https://openalex.org/I4210147685"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":["https://openalex.org/A5070019572"],"corresponding_institution_ids":["https://openalex.org/I4210147685"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":0.2048,"has_fulltext":false,"cited_by_count":2,"citation_normalized_percentile":{"value":0.29549364,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":93,"max":95},"biblio":{"volume":"28","issue":"7","first_page":"2724","last_page":"2731"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T11281","display_name":"Asymmetric Hydrogenation and Catalysis","score":0.9984999895095825,"subfield":{"id":"https://openalex.org/subfields/1604","display_name":"Inorganic 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/T11281","display_name":"Asymmetric Hydrogenation and Catalysis","score":0.9984999895095825,"subfield":{"id":"https://openalex.org/subfields/1604","display_name":"Inorganic 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/T10013","display_name":"Asymmetric Synthesis and Catalysis","score":0.0010999999940395355,"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/T10404","display_name":"Enzyme Catalysis and Immobilization","score":0.0,"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"}}],"keywords":[{"id":"https://openalex.org/keywords/asymmetric-reductive-amination","display_name":"asymmetric reductive amination","score":0.9980000257492065},{"id":"https://openalex.org/keywords/asymmetric-hydrogenation","display_name":"asymmetric hydrogenation","score":0.699999988079071},{"id":"https://openalex.org/keywords/primary-amines","display_name":"primary amines","score":0.5950000286102295},{"id":"https://openalex.org/keywords/high-throughput-screening","display_name":"high-throughput screening","score":0.7129999995231628},{"id":"https://openalex.org/keywords/diastereomeric-salts","display_name":"diastereomeric salts","score":0.7289999723434448},{"id":"https://openalex.org/keywords/l-tartaric-acid","display_name":"L-tartaric acid","score":0.8930000066757202}],"concepts":[{"id":"https://openalex.org/C2779938440","wikidata":"https://www.wikidata.org/wiki/Q549876","display_name":"Reductive amination","level":3,"score":0.9558494091033936},{"id":"https://openalex.org/C131779359","wikidata":"https://www.wikidata.org/wiki/Q471875","display_name":"Amine gas treating","level":2,"score":0.7613621354103088},{"id":"https://openalex.org/C198503264","wikidata":"https://www.wikidata.org/wiki/Q471635","display_name":"Amination","level":3,"score":0.7388544082641602},{"id":"https://openalex.org/C2777738585","wikidata":"https://www.wikidata.org/wiki/Q170744","display_name":"Ketone","level":2,"score":0.7255916595458984},{"id":"https://openalex.org/C2777977315","wikidata":"https://www.wikidata.org/wiki/Q7243056","display_name":"Primary (astronomy)","level":2,"score":0.7247563004493713},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.6719401478767395},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.5972762107849121},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.3809860944747925},{"id":"https://openalex.org/C188027245","wikidata":"https://www.wikidata.org/wiki/Q750446","display_name":"Polymer chemistry","level":1,"score":0.3250102698802948},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.14493656158447266},{"id":"https://openalex.org/C1276947","wikidata":"https://www.wikidata.org/wiki/Q333","display_name":"Astronomy","level":1,"score":0.0},{"id":"https://openalex.org/C121332964","wikidata":"https://www.wikidata.org/wiki/Q413","display_name":"Physics","level":0,"score":0.0}],"mesh":[],"locations_count":1,"locations":[{"id":"doi:10.1021/acs.oprd.4c00095","doi":"https://doi.org/10.1021/acs.oprd.4c00095","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.oprd.4c00095","pdf_url":null,"source":{"id":"https://openalex.org/S107255770","display_name":"Organic Process Research & Development","issn_l":"1083-6160","issn":["1083-6160","1520-586X"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-b","jufo-1","norway-1","poland-100","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Organic Process Research &amp; Development","raw_type":"journal-article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":30,"referenced_works":["https://openalex.org/W2000063610","https://openalex.org/W2001669723","https://openalex.org/W2009884940","https://openalex.org/W2033556576","https://openalex.org/W2052290488","https://openalex.org/W2077516083","https://openalex.org/W2093414987","https://openalex.org/W2123818560","https://openalex.org/W2124680160","https://openalex.org/W2168679251","https://openalex.org/W2174182506","https://openalex.org/W2300247830","https://openalex.org/W2331479592","https://openalex.org/W2440655386","https://openalex.org/W2521585712","https://openalex.org/W2730740418","https://openalex.org/W2769763900","https://openalex.org/W2772865069","https://openalex.org/W2787833273","https://openalex.org/W2901704291","https://openalex.org/W2921540193","https://openalex.org/W2944148756","https://openalex.org/W2949845925","https://openalex.org/W3144592352","https://openalex.org/W3208795778","https://openalex.org/W4226336197","https://openalex.org/W4281885601","https://openalex.org/W4311877636","https://openalex.org/W4367185707","https://openalex.org/W4383535833"],"related_works":["https://openalex.org/W3034581495","https://openalex.org/W3118505984","https://openalex.org/W3200334448","https://openalex.org/W4409366350","https://openalex.org/W2163868434","https://openalex.org/W2949109919","https://openalex.org/W4254749619","https://openalex.org/W2027941598","https://openalex.org/W3043069575","https://openalex.org/W2787833273"],"abstract_inverted_index":{"Direct":[0],"asymmetric":[1],"reductive":[2],"amination":[3],"provides":[4],"a":[5,16,45,51],"straightforward":[6],"approach":[7],"to":[8,19,86,91],"preparing":[9],"\u03b1-chiral":[10,21],"amine":[11,23,75,101],"synthons.":[12],"We":[13],"herein":[14],"disclose":[15],"chemical":[17],"process":[18],"produce":[20],"secondary":[22,100],"from":[24,71],"alkyl":[25],"(hetero)aryl":[26],"ketone,":[27],"primary":[28],"amine,":[29],"and":[30,50,80,88],"molecular":[31],"hydrogen.":[32],"By":[33],"using":[34],"high-throughput":[35],"screening":[36],"technology,":[37],"an":[38,97],"iridium/bisphosphine":[39],"catalyst":[40],"was":[41,102],"selected":[42],"that":[43],"gives":[44],"turnover":[46],"number":[47],"of":[48,54,59,68,96],"\u223c1000":[49],"ee":[52,84],"value":[53,85],"91\u201392%":[55],"in":[56],"the":[57,72,83,89],"production":[58,95],"(":[60,63],"R":[61],")-2-((1-(2-(bis(4-methoxybenzyl)amino)pyridin-3-yl)ethyl)amino)ethan-1-ol":[62],"1":[64],").":[65],"The":[66,93],"formation":[67],"diastereomeric":[69],"salt":[70],"crude":[73],"chiral":[74,99],"with":[76,104,107],"L":[77],"-tartaric":[78],"acid":[79],"crystallization":[81],"upgrade":[82],">99%":[87],"purity":[90],">99%.":[92],"multikilogram":[94],"enantiopure":[98],"realized":[103],"good":[105],"reproducibility":[106],"this":[108],"process.":[109]},"counts_by_year":[{"year":2025,"cited_by_count":2}],"updated_date":"2026-10-16T09:59:22.235173","created_date":"2024-05-23T00:00:00"}
