{"id":"https://openalex.org/W4317871237","doi":"https://doi.org/10.1021/acs.orglett.2c04161","title":"Cu-Catalyzed Cross-Electrophilic Coupling of \u03b1-Diazoesters with O-Benzoyl Hydroxylamines for the Synthesis of Unnatural N-Alkyl \u03b1-Amino Acid Derivatives","display_name":"Cu-Catalyzed Cross-Electrophilic Coupling of \u03b1-Diazoesters with O-Benzoyl Hydroxylamines for the Synthesis of Unnatural N-Alkyl \u03b1-Amino Acid Derivatives","publication_year":2023,"publication_date":"2023-01-24","ids":{"openalex":"https://openalex.org/W4317871237","doi":"https://doi.org/10.1021/acs.orglett.2c04161","pmid":"https://pubmed.ncbi.nlm.nih.gov/36692243"},"language":"en","primary_location":{"id":"doi:10.1021/acs.orglett.2c04161","doi":"https://doi.org/10.1021/acs.orglett.2c04161","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.orglett.2c04161","pdf_url":null,"source":{"id":"https://openalex.org/S201989124","display_name":"Organic Letters","issn_l":"1523-7052","issn":["1523-7052","1523-7060"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-2","ki-jl-2","medline","norway-2","poland-140","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 Letters","raw_type":"journal-article"},"volume":null,"type":"article","is_traditional":true,"indexed_in":["crossref","pubmed"],"open_access":{"is_oa":true,"oa_status":"green","oa_url":"http://ira.lib.polyu.edu.hk/bitstream/10397/97193/1/Cu-amine-OL_R16_WYY.pdf","any_repository_has_fulltext":true},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5025649159","display_name":"Yiu-Wai Yeung","orcid":"https://orcid.org/0000-0001-7678-8963","observed_orcids":["https://orcid.org/0000-0001-7678-8963"]},"institutions":[{"id":"https://openalex.org/I14243506","display_name":"Hong Kong Polytechnic University","ror":"https://ror.org/0030zas98","country_code":"HK","type":"education","lineage":["https://openalex.org/I14243506"]}],"countries":["HK"],"is_corresponding":false,"raw_author_name":"Yiu-Wai Yeung","raw_affiliation_strings":["State Key Laboratory of Chemical Biology and Drug Discovery, Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong"],"raw_orcid":"https://orcid.org/0000-0001-7678-8963","affiliations":[{"raw_affiliation_string":"State Key Laboratory of Chemical Biology and Drug Discovery, Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong","institution_ids":["https://openalex.org/I14243506"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5030730368","display_name":"Chun\u2010Ming Chan","orcid":"https://orcid.org/0000-0003-3859-8477","observed_orcids":["https://orcid.org/0000-0003-3859-8477"]},"institutions":[{"id":"https://openalex.org/I14243506","display_name":"Hong Kong Polytechnic University","ror":"https://ror.org/0030zas98","country_code":"HK","type":"education","lineage":["https://openalex.org/I14243506"]}],"countries":["HK"],"is_corresponding":false,"raw_author_name":"Chun-Ming Chan","raw_affiliation_strings":["State Key Laboratory of Chemical Biology and Drug Discovery, Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong"],"raw_orcid":"https://orcid.org/0000-0003-3859-8477","affiliations":[{"raw_affiliation_string":"State Key Laboratory of Chemical Biology and Drug Discovery, Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong","institution_ids":["https://openalex.org/I14243506"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5088393616","display_name":"Yuting Chen","orcid":"https://orcid.org/0000-0001-5549-5387","observed_orcids":["https://orcid.org/0000-0001-5549-5387","https://orcid.org/0009-0002-4091-298X"]},"institutions":[{"id":"https://openalex.org/I14243506","display_name":"Hong Kong Polytechnic University","ror":"https://ror.org/0030zas98","country_code":"HK","type":"education","lineage":["https://openalex.org/I14243506"]}],"countries":["HK"],"is_corresponding":false,"raw_author_name":"Yu-Ting Chen","raw_affiliation_strings":["State Key Laboratory of Chemical Biology and Drug Discovery, Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"State Key Laboratory of Chemical Biology and Drug Discovery, Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong","institution_ids":["https://openalex.org/I14243506"]}]},{"author_position":"middle","author":{"id":null,"display_name":"Marco Chan","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I14243506","display_name":"Hong Kong Polytechnic University","ror":"https://ror.org/0030zas98","country_code":"HK","type":"education","lineage":["https://openalex.org/I14243506"]}],"countries":["HK"],"is_corresponding":false,"raw_author_name":"Marco Chan","raw_affiliation_strings":["State Key Laboratory of Chemical Biology and Drug Discovery, Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"State Key Laboratory of Chemical Biology and Drug Discovery, Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong","institution_ids":["https://openalex.org/I14243506"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5102759622","display_name":"Mingyu Luo","orcid":"https://orcid.org/0009-0008-4965-0852","observed_orcids":["https://orcid.org/0009-0008-4965-0852","https://orcid.org/0009-0003-6883-4474"]},"institutions":[{"id":"https://openalex.org/I14243506","display_name":"Hong Kong Polytechnic University","ror":"https://ror.org/0030zas98","country_code":"HK","type":"education","lineage":["https://openalex.org/I14243506"]}],"countries":["HK"],"is_corresponding":false,"raw_author_name":"Mingyu Luo","raw_affiliation_strings":["State Key Laboratory of Chemical Biology and Drug Discovery, Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"State Key Laboratory of Chemical Biology and Drug Discovery, Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong","institution_ids":["https://openalex.org/I14243506"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5087727205","display_name":"Xin Rui Gao","orcid":"https://orcid.org/0000-0001-7162-4177","observed_orcids":["https://orcid.org/0000-0001-7162-4177"]},"institutions":[{"id":"https://openalex.org/I152031979","display_name":"Nanjing Normal University","ror":"https://ror.org/036trcv74","country_code":"CN","type":"education","lineage":["https://openalex.org/I152031979"]}],"countries":["CN"],"is_corresponding":false,"raw_author_name":"Xin Gao","raw_affiliation_strings":["School of Food Science and Pharmaceutical Engineering, Nanjing Normal University, Nanjing 210098, China"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"School of Food Science and Pharmaceutical Engineering, Nanjing Normal University, Nanjing 210098, China","institution_ids":["https://openalex.org/I152031979"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5060949125","display_name":"Bingnan Du","orcid":"https://orcid.org/0000-0001-5503-3916","observed_orcids":["https://orcid.org/0000-0001-5503-3916"]},"institutions":[{"id":"https://openalex.org/I152031979","display_name":"Nanjing Normal University","ror":"https://ror.org/036trcv74","country_code":"CN","type":"education","lineage":["https://openalex.org/I152031979"]}],"countries":["CN"],"is_corresponding":true,"raw_author_name":"Bingnan Du","raw_affiliation_strings":["School of Food Science and Pharmaceutical Engineering, Nanjing Normal University, Nanjing 210098, China"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"School of Food Science and Pharmaceutical Engineering, Nanjing Normal University, Nanjing 210098, China","institution_ids":["https://openalex.org/I152031979"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5076210525","display_name":"Wing\u2010Yiu Yu","orcid":"https://orcid.org/0000-0003-3181-8908","observed_orcids":["https://orcid.org/0000-0003-3181-8908"]},"institutions":[{"id":"https://openalex.org/I14243506","display_name":"Hong Kong Polytechnic University","ror":"https://ror.org/0030zas98","country_code":"HK","type":"education","lineage":["https://openalex.org/I14243506"]}],"countries":["HK"],"is_corresponding":true,"raw_author_name":"Wing-Yiu Yu","raw_affiliation_strings":["State Key Laboratory of Chemical Biology and Drug Discovery, Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong"],"raw_orcid":"https://orcid.org/0000-0003-3181-8908","affiliations":[{"raw_affiliation_string":"State Key Laboratory of Chemical Biology and Drug Discovery, Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong","institution_ids":["https://openalex.org/I14243506"]}]}],"institutions":[],"countries_distinct_count":2,"institutions_distinct_count":2,"corresponding_author_ids":["https://openalex.org/A5060949125","https://openalex.org/A5076210525"],"corresponding_institution_ids":["https://openalex.org/I14243506","https://openalex.org/I152031979"],"apc_list":{"value":5000,"currency":"USD","value_usd":5000},"apc_paid":null,"fwci":0.8758,"has_fulltext":true,"cited_by_count":9,"citation_normalized_percentile":{"value":0.63465363,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":88,"max":97},"biblio":{"volume":"25","issue":"4","first_page":"619","last_page":"623"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T11611","display_name":"Cyclopropane Reaction Mechanisms","score":0.8515999913215637,"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/T11611","display_name":"Cyclopropane Reaction Mechanisms","score":0.8515999913215637,"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/T10701","display_name":"Radical Photochemical Reactions","score":0.052799999713897705,"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/T10548","display_name":"Catalytic Cross-Coupling Reactions","score":0.0430000014603138,"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/copper-catalysis","display_name":"copper catalysis","score":0.9359999895095825},{"id":"https://openalex.org/keywords/alpha-diazoesters","display_name":"\u03b1-diazoesters","score":0.9909999966621399},{"id":"https://openalex.org/keywords/unnatural-amino-acids","display_name":"unnatural amino acids","score":0.8289999961853027},{"id":"https://openalex.org/keywords/nitrogen-centered-radicals","display_name":"nitrogen-centered radicals","score":0.6890000104904175}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9416338205337524},{"id":"https://openalex.org/C50027330","wikidata":"https://www.wikidata.org/wiki/Q908086","display_name":"Electrophile","level":3,"score":0.7849009037017822},{"id":"https://openalex.org/C2776904781","wikidata":"https://www.wikidata.org/wiki/Q424424","display_name":"Diazo","level":2,"score":0.7773630619049072},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.7453842163085938},{"id":"https://openalex.org/C2780263894","wikidata":"https://www.wikidata.org/wiki/Q335268","display_name":"Alkyl","level":2,"score":0.6237209439277649},{"id":"https://openalex.org/C40875361","wikidata":"https://www.wikidata.org/wiki/Q2356542","display_name":"Reagent","level":2,"score":0.5670499205589294},{"id":"https://openalex.org/C2777961443","wikidata":"https://www.wikidata.org/wiki/Q106520","display_name":"Hydride","level":3,"score":0.5631659030914307},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.48079267144203186},{"id":"https://openalex.org/C2780112151","wikidata":"https://www.wikidata.org/wiki/Q412033","display_name":"Trifluoroacetic acid","level":2,"score":0.4706646203994751},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.4556853771209717},{"id":"https://openalex.org/C139066938","wikidata":"https://www.wikidata.org/wiki/Q185056","display_name":"Radical","level":2,"score":0.43894538283348083},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.3763800263404846},{"id":"https://openalex.org/C544153396","wikidata":"https://www.wikidata.org/wiki/Q11426","display_name":"Metal","level":2,"score":0.07961565256118774}],"mesh":[],"locations_count":3,"locations":[{"id":"doi:10.1021/acs.orglett.2c04161","doi":"https://doi.org/10.1021/acs.orglett.2c04161","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.orglett.2c04161","pdf_url":null,"source":{"id":"https://openalex.org/S201989124","display_name":"Organic Letters","issn_l":"1523-7052","issn":["1523-7052","1523-7060"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-2","ki-jl-2","medline","norway-2","poland-140","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 Letters","raw_type":"journal-article"},{"id":"pmid:36692243","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/36692243","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 letters","raw_type":"Journal Article"},{"id":"pmh:oai:ira.lib.polyu.edu.hk:10397/97193","doi":null,"is_oa":true,"landing_page_url":"http://hdl.handle.net/10397/97193","pdf_url":"http://ira.lib.polyu.edu.hk/bitstream/10397/97193/1/Cu-amine-OL_R16_WYY.pdf","source":{"id":"https://openalex.org/S4306400205","display_name":"PolyU Institutional Research Archive (Hong Kong Polytechnic University)","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I14243506","host_organization_name":"Hong Kong Polytechnic University","host_organization_lineage":["https://openalex.org/I14243506"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":null,"raw_type":"Journal/Magazine Article"}],"best_oa_location":{"id":"pmh:oai:ira.lib.polyu.edu.hk:10397/97193","doi":null,"is_oa":true,"landing_page_url":"http://hdl.handle.net/10397/97193","pdf_url":"http://ira.lib.polyu.edu.hk/bitstream/10397/97193/1/Cu-amine-OL_R16_WYY.pdf","source":{"id":"https://openalex.org/S4306400205","display_name":"PolyU Institutional Research Archive (Hong Kong Polytechnic University)","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I14243506","host_organization_name":"Hong Kong Polytechnic University","host_organization_lineage":["https://openalex.org/I14243506"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":null,"raw_type":"Journal/Magazine Article"},"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G6586781700","display_name":null,"funder_award_id":"PolyU153017/19P","funder_id":"https://openalex.org/F4320321592","funder_display_name":"Research Grants Council, University Grants Committee"},{"id":"https://openalex.org/G8416535204","display_name":null,"funder_award_id":"PolyU153034/20P","funder_id":"https://openalex.org/F4320321592","funder_display_name":"Research Grants Council, University Grants Committee"}],"funders":[{"id":"https://openalex.org/F4320321592","display_name":"Research Grants Council, University Grants Committee","ror":"https://ror.org/00djwmt25"},{"id":"https://openalex.org/F4320322598","display_name":"Hong Kong Polytechnic University","ror":"https://ror.org/0030zas98"}],"has_content":{"grobid_xml":true,"pdf":true},"content_urls":{"pdf":"https://content.openalex.org/works/W4317871237.pdf","grobid_xml":"https://content.openalex.org/works/W4317871237.grobid-xml"},"referenced_works_count":29,"referenced_works":["https://openalex.org/W583301826","https://openalex.org/W1966508946","https://openalex.org/W1966930861","https://openalex.org/W1967419891","https://openalex.org/W1984232099","https://openalex.org/W2020320704","https://openalex.org/W2029617469","https://openalex.org/W2053089772","https://openalex.org/W2110709874","https://openalex.org/W2112398510","https://openalex.org/W2148056939","https://openalex.org/W2151228173","https://openalex.org/W2157180124","https://openalex.org/W2318444114","https://openalex.org/W2324081872","https://openalex.org/W2328379508","https://openalex.org/W2334919103","https://openalex.org/W2399980361","https://openalex.org/W2516283850","https://openalex.org/W2601118842","https://openalex.org/W2753149014","https://openalex.org/W2766669879","https://openalex.org/W2793503252","https://openalex.org/W2903740635","https://openalex.org/W2952878492","https://openalex.org/W2991545174","https://openalex.org/W3005775246","https://openalex.org/W4220727926","https://openalex.org/W4280500953"],"related_works":["https://openalex.org/W2555405337","https://openalex.org/W2912395301","https://openalex.org/W3155174389","https://openalex.org/W2919784442","https://openalex.org/W2806294779","https://openalex.org/W2103447686","https://openalex.org/W4375860547","https://openalex.org/W6944703890","https://openalex.org/W2952746797","https://openalex.org/W4402284482"],"abstract_inverted_index":{"We":[0],"describe":[1],"a":[2,43,69],"Cu-catalyzed":[3],"cross-electrophilic":[4],"coupling":[5],"reaction":[6],"for":[7],"synthesizing":[8],"\u03b1-amino":[9,75],"acid":[10,76],"derivatives":[11],"from":[12,53],"\u03b1-diazoesters":[13],"with":[14,18,60],"O":[15],"-benzoyl":[16],"hydroxylamines":[17],"Cu(OAc)":[19],"2":[20],"as":[21,27,40],"the":[22,28,41,54,61],"catalyst":[23],"and":[24,71],"polymethylhydrosilane":[25],"(PMHS)":[26],"hydride":[29],"reagent.":[30],"Excellent":[31],"functional":[32],"group":[33],"compatibilities":[34],"were":[35],"demonstrated.":[36],"With":[37],"ethyl":[38],"2-diazo-3-oxobutanoate":[39],"precursor,":[42],"Cu-acetoacetate":[44],"complex":[45],"has":[46],"been":[47],"characterized":[48],"by":[49],"ESI-MS":[50],"analysis.":[51],"Results":[52],"radical":[55],"trap":[56],"experiments":[57],"are":[58],"consistent":[59],"intermediacy":[62],"of":[63,74],"nitrogen-centered":[64],"radicals.":[65],"This":[66],"strategy":[67],"offers":[68],"simple":[70],"inexpensive":[72],"synthesis":[73],"derivatives.":[77]},"counts_by_year":[{"year":2026,"cited_by_count":3},{"year":2025,"cited_by_count":3},{"year":2024,"cited_by_count":2},{"year":2023,"cited_by_count":1}],"updated_date":"2026-10-03T13:16:28.481748","created_date":"2023-01-25T00:00:00"}