{"id":"https://openalex.org/W4367185707","doi":"https://doi.org/10.1021/acs.oprd.3c00088","title":"Ruthenium-Catalyzed Direct Asymmetric Reductive Amination for the Synthesis of a Chiral Primary Amine Intermediate En Route to a PDE2A Inhibitor, TAK-915","display_name":"Ruthenium-Catalyzed Direct Asymmetric Reductive Amination for the Synthesis of a Chiral Primary Amine Intermediate En Route to a PDE2A Inhibitor, TAK-915","publication_year":2023,"publication_date":"2023-04-27","ids":{"openalex":"https://openalex.org/W4367185707","doi":"https://doi.org/10.1021/acs.oprd.3c00088"},"language":"en","primary_location":{"id":"doi:10.1021/acs.oprd.3c00088","doi":"https://doi.org/10.1021/acs.oprd.3c00088","is_oa":true,"landing_page_url":"https://doi.org/10.1021/acs.oprd.3c00088","pdf_url":"https://pubs.acs.org/doi/pdf/10.1021/acs.oprd.3c00088","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":"cc-by-nc-nd","license_id":"https://openalex.org/licenses/cc-by-nc-nd","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Organic Process Research &amp; Development","raw_type":"journal-article"},"volume":null,"type":"article","indexed_in":["crossref"],"open_access":{"is_oa":true,"oa_status":"hybrid","oa_url":"https://pubs.acs.org/doi/pdf/10.1021/acs.oprd.3c00088","any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5077132957","display_name":"Masatoshi Yamada","orcid":"https://orcid.org/0000-0002-8390-6021","observed_orcids":["https://orcid.org/0000-0002-8390-6021"]},"institutions":[{"id":"https://openalex.org/I44892455","display_name":"Takeda (Japan)","ror":"https://ror.org/04hjbmv12","country_code":"JP","type":"company","lineage":["https://openalex.org/I44892455"]}],"countries":["JP"],"is_corresponding":true,"raw_author_name":"Masatoshi Yamada","raw_affiliation_strings":["Process Chemistry, Pharmaceutical Sciences, Takeda Pharmaceutical Company Limited, 17-85, Jusohonmachi 2-chome, Yodogawa-ku, Osaka 532-8686, Japan"],"raw_orcid":"https://orcid.org/0000-0002-8390-6021","affiliations":[{"raw_affiliation_string":"Process Chemistry, Pharmaceutical Sciences, Takeda Pharmaceutical Company Limited, 17-85, Jusohonmachi 2-chome, Yodogawa-ku, Osaka 532-8686, Japan","institution_ids":["https://openalex.org/I44892455"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5038911748","display_name":"Koichi Murai","orcid":"https://orcid.org/0000-0001-8973-7196","observed_orcids":["https://orcid.org/0000-0001-8973-7196"]},"institutions":[{"id":"https://openalex.org/I44892455","display_name":"Takeda (Japan)","ror":"https://ror.org/04hjbmv12","country_code":"JP","type":"company","lineage":["https://openalex.org/I44892455"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Koichi Murai","raw_affiliation_strings":["Process Chemistry, Pharmaceutical Sciences, Takeda Pharmaceutical Company Limited, 17-85, Jusohonmachi 2-chome, Yodogawa-ku, Osaka 532-8686, Japan"],"raw_orcid":"https://orcid.org/0000-0001-8973-7196","affiliations":[{"raw_affiliation_string":"Process Chemistry, Pharmaceutical Sciences, Takeda Pharmaceutical Company Limited, 17-85, Jusohonmachi 2-chome, Yodogawa-ku, Osaka 532-8686, Japan","institution_ids":["https://openalex.org/I44892455"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5016304577","display_name":"Kotaro Yamaguchi","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I44892455","display_name":"Takeda (Japan)","ror":"https://ror.org/04hjbmv12","country_code":"JP","type":"company","lineage":["https://openalex.org/I44892455"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Kotaro Yamaguchi","raw_affiliation_strings":["Process Chemistry, Pharmaceutical Sciences, Takeda Pharmaceutical Company Limited, 17-85, Jusohonmachi 2-chome, Yodogawa-ku, Osaka 532-8686, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Process Chemistry, Pharmaceutical Sciences, Takeda Pharmaceutical Company Limited, 17-85, Jusohonmachi 2-chome, Yodogawa-ku, Osaka 532-8686, Japan","institution_ids":["https://openalex.org/I44892455"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5009737170","display_name":"Mitsuhisa Yamano","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I44892455","display_name":"Takeda (Japan)","ror":"https://ror.org/04hjbmv12","country_code":"JP","type":"company","lineage":["https://openalex.org/I44892455"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Mitsuhisa Yamano","raw_affiliation_strings":["Process Chemistry, Pharmaceutical Sciences, Takeda Pharmaceutical Company Limited, 17-85, Jusohonmachi 2-chome, Yodogawa-ku, Osaka 532-8686, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Process Chemistry, Pharmaceutical Sciences, Takeda Pharmaceutical Company Limited, 17-85, Jusohonmachi 2-chome, Yodogawa-ku, Osaka 532-8686, Japan","institution_ids":["https://openalex.org/I44892455"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":["https://openalex.org/A5077132957"],"corresponding_institution_ids":["https://openalex.org/I44892455"],"apc_list":{"value":5000,"currency":"USD","value_usd":5000},"apc_paid":{"value":5000,"currency":"USD","value_usd":5000},"fwci":0.6998,"has_fulltext":false,"cited_by_count":9,"citation_normalized_percentile":{"value":0.61188404,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":89,"max":98},"biblio":{"volume":"27","issue":"5","first_page":"972","last_page":"981"},"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":0.0012000000569969416,"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/T10092","display_name":"Organometallic Complex Synthesis and Catalysis","score":0.0,"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/ruthenium-catalysis","display_name":"ruthenium catalysis","score":0.9300000071525574},{"id":"https://openalex.org/keywords/asymmetric-reductive-amination","display_name":"asymmetric reductive amination","score":0.9950000047683716},{"id":"https://openalex.org/keywords/chiral-primary-amines","display_name":"chiral primary amines","score":0.7760000228881836},{"id":"https://openalex.org/keywords/alpha-alkoxy-ketones","display_name":"\u03b1-alkoxy ketones","score":0.9520000219345093},{"id":"https://openalex.org/keywords/asymmetric-synthesis","display_name":"asymmetric synthesis","score":0.5289999842643738},{"id":"https://openalex.org/keywords/air-and-moisture-stable-catalysts","display_name":"air- and moisture-stable catalysts","score":0.7839999794960022}],"concepts":[{"id":"https://openalex.org/C2779938440","wikidata":"https://www.wikidata.org/wiki/Q549876","display_name":"Reductive amination","level":3,"score":0.9112300276756287},{"id":"https://openalex.org/C555196967","wikidata":"https://www.wikidata.org/wiki/Q1086","display_name":"Ruthenium","level":3,"score":0.8618878126144409},{"id":"https://openalex.org/C131779359","wikidata":"https://www.wikidata.org/wiki/Q471875","display_name":"Amine gas treating","level":2,"score":0.7397451400756836},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.6803920865058899},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.660201907157898},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.6389576196670532},{"id":"https://openalex.org/C40875361","wikidata":"https://www.wikidata.org/wiki/Q2356542","display_name":"Reagent","level":2,"score":0.6305418014526367},{"id":"https://openalex.org/C198503264","wikidata":"https://www.wikidata.org/wiki/Q471635","display_name":"Amination","level":3,"score":0.6249216198921204},{"id":"https://openalex.org/C90150868","wikidata":"https://www.wikidata.org/wiki/Q39513","display_name":"Alkoxy group","level":3,"score":0.5313202738761902},{"id":"https://openalex.org/C2777977315","wikidata":"https://www.wikidata.org/wiki/Q7243056","display_name":"Primary (astronomy)","level":2,"score":0.4752117097377777},{"id":"https://openalex.org/C2777738585","wikidata":"https://www.wikidata.org/wiki/Q170744","display_name":"Ketone","level":2,"score":0.4286731481552124},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.41354191303253174},{"id":"https://openalex.org/C1276947","wikidata":"https://www.wikidata.org/wiki/Q333","display_name":"Astronomy","level":1,"score":0.0},{"id":"https://openalex.org/C2780263894","wikidata":"https://www.wikidata.org/wiki/Q335268","display_name":"Alkyl","level":2,"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.3c00088","doi":"https://doi.org/10.1021/acs.oprd.3c00088","is_oa":true,"landing_page_url":"https://doi.org/10.1021/acs.oprd.3c00088","pdf_url":"https://pubs.acs.org/doi/pdf/10.1021/acs.oprd.3c00088","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":"cc-by-nc-nd","license_id":"https://openalex.org/licenses/cc-by-nc-nd","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Organic Process Research &amp; Development","raw_type":"journal-article"}],"best_oa_location":{"id":"doi:10.1021/acs.oprd.3c00088","doi":"https://doi.org/10.1021/acs.oprd.3c00088","is_oa":true,"landing_page_url":"https://doi.org/10.1021/acs.oprd.3c00088","pdf_url":"https://pubs.acs.org/doi/pdf/10.1021/acs.oprd.3c00088","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":"cc-by-nc-nd","license_id":"https://openalex.org/licenses/cc-by-nc-nd","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Organic Process Research &amp; Development","raw_type":"journal-article"},"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[],"has_content":{"pdf":true,"grobid_xml":false},"content_urls":{"pdf":"https://content.openalex.org/works/W4367185707.pdf"},"referenced_works_count":45,"referenced_works":["https://openalex.org/W1974796841","https://openalex.org/W1988488306","https://openalex.org/W2014046033","https://openalex.org/W2017374200","https://openalex.org/W2025861611","https://openalex.org/W2026145553","https://openalex.org/W2026245921","https://openalex.org/W2026529043","https://openalex.org/W2027941598","https://openalex.org/W2030388466","https://openalex.org/W2033664830","https://openalex.org/W2052290488","https://openalex.org/W2058841148","https://openalex.org/W2080167374","https://openalex.org/W2083912982","https://openalex.org/W2300247830","https://openalex.org/W2316062356","https://openalex.org/W2325479400","https://openalex.org/W2328521607","https://openalex.org/W2331479592","https://openalex.org/W2346867767","https://openalex.org/W2510400385","https://openalex.org/W2600849036","https://openalex.org/W2730740418","https://openalex.org/W2740842268","https://openalex.org/W2745269613","https://openalex.org/W2772865069","https://openalex.org/W2787833273","https://openalex.org/W2889556143","https://openalex.org/W2889839718","https://openalex.org/W2921540193","https://openalex.org/W2949845925","https://openalex.org/W2950590046","https://openalex.org/W2982161494","https://openalex.org/W2999685166","https://openalex.org/W3003423641","https://openalex.org/W3034581495","https://openalex.org/W3043655164","https://openalex.org/W3118505984","https://openalex.org/W3155789185","https://openalex.org/W3185305066","https://openalex.org/W3208795778","https://openalex.org/W3216319240","https://openalex.org/W4221098370","https://openalex.org/W4312063446"],"related_works":["https://openalex.org/W2787833273","https://openalex.org/W3118505984","https://openalex.org/W3034581495","https://openalex.org/W4249782434","https://openalex.org/W2336569186","https://openalex.org/W4282979392","https://openalex.org/W6925347489","https://openalex.org/W2772865069","https://openalex.org/W3193987075","https://openalex.org/W2799499172"],"abstract_inverted_index":{"High":[0],"Resolution":[1],"Image":[2],"Download":[3],"MS":[4],"PowerPoint":[5],"Slide":[6],"Here,":[7],"we":[8],"report":[9],"a":[10,22,34,42,68,83],"novel,":[11],"efficient":[12],"ruthenium-catalyzed":[13],"direct":[14],"asymmetric":[15],"reductive":[16],"amination":[17],"of":[18,41],"an":[19,78],"\u03b1-alkoxy":[20],"ketone,":[21],"structural":[23],"motif":[24],"for":[25,82],"which":[26],"it":[27],"is":[28],"more":[29],"challenging":[30],"to":[31,50,67,76],"implement":[32],"such":[33],"transformation":[35],"than":[36],"1,3-dicarbonyl":[37],"compounds.":[38],"The":[39],"discovery":[40],"novel":[43],"ruthenium":[44],"catalyst":[45],"that":[46],"was":[47],"highly":[48],"stable":[49],"air":[51],"and":[52],"moisture,":[53],"as":[54,56],"well":[55],"being":[57],"readily":[58],"prepared":[59],"from":[60],"commercially":[61],"available":[62],"reagents,":[63],"enabled":[64],"rapid":[65],"access":[66],"key":[69],"synthetic":[70],"chiral":[71],"primary":[72],"amine":[73],"en":[74],"route":[75],"TAK-915,":[77],"active":[79],"pharmaceutical":[80],"ingredient":[81],"PDE2A":[84],"inhibitor.":[85]},"counts_by_year":[{"year":2026,"cited_by_count":3},{"year":2025,"cited_by_count":1},{"year":2024,"cited_by_count":4},{"year":2023,"cited_by_count":1}],"updated_date":"2026-08-28T12:50:07.497085","created_date":"2023-04-28T00:00:00"}
