{"id":"https://openalex.org/W4411583582","doi":"https://doi.org/10.1021/jacs.5c07821","title":"Enantioselective Synthesis of 2,3-Disubstituted Azetidines via Copper-Catalyzed Boryl Allylation of Azetines","display_name":"Enantioselective Synthesis of 2,3-Disubstituted Azetidines via Copper-Catalyzed Boryl Allylation of Azetines","publication_year":2025,"publication_date":"2025-06-24","ids":{"openalex":"https://openalex.org/W4411583582","doi":"https://doi.org/10.1021/jacs.5c07821","pmid":"https://pubmed.ncbi.nlm.nih.gov/40553580"},"language":"en","primary_location":{"id":"doi:10.1021/jacs.5c07821","doi":"https://doi.org/10.1021/jacs.5c07821","is_oa":true,"landing_page_url":"https://doi.org/10.1021/jacs.5c07821","pdf_url":"https://pubs.acs.org/doi/pdf/10.1021/jacs.5c07821?ref=article_openPDF","source":{"id":"https://openalex.org/S111155417","display_name":"Journal of the American Chemical Society","issn_l":"0002-7863","issn":["0002-7863","1520-5126","1943-2984"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","jufo-3","ki-jl-3","medline","norway-2"],"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","license_id":"https://openalex.org/licenses/cc-by","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of the American Chemical Society","raw_type":"journal-article"},"volume":null,"type":"article","indexed_in":["crossref","pubmed"],"open_access":{"is_oa":true,"oa_status":"hybrid","oa_url":"https://pubs.acs.org/doi/pdf/10.1021/jacs.5c07821?ref=article_openPDF","any_repository_has_fulltext":true},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5089479809","display_name":"Minghui Zhu","orcid":"https://orcid.org/0000-0003-2251-1496","observed_orcids":["https://orcid.org/0000-0003-2251-1496","https://orcid.org/0009-0003-1963-6316"]},"institutions":[{"id":"https://openalex.org/I200769079","display_name":"Hong Kong University of Science and Technology","ror":"https://ror.org/00q4vv597","country_code":"HK","type":"education","lineage":["https://openalex.org/I200769079"]}],"countries":["HK"],"is_corresponding":false,"raw_author_name":"Minghui Zhu","raw_affiliation_strings":["Department of Chemistry and the Hong Kong Branch of Chinese National Engineering Research Centre for Tissue Restoration & Reconstruction, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR 999077, China"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry and the Hong Kong Branch of Chinese National Engineering Research Centre for Tissue Restoration & Reconstruction, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR 999077, China","institution_ids":["https://openalex.org/I200769079"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5024502174","display_name":"Jianwei Sun","orcid":"https://orcid.org/0000-0002-2470-1077","observed_orcids":["https://orcid.org/0000-0002-2470-1077"]},"institutions":[{"id":"https://openalex.org/I200769079","display_name":"Hong Kong University of Science and Technology","ror":"https://ror.org/00q4vv597","country_code":"HK","type":"education","lineage":["https://openalex.org/I200769079"]}],"countries":["HK"],"is_corresponding":true,"raw_author_name":"Jianwei Sun","raw_affiliation_strings":["Department of Chemistry and the Hong Kong Branch of Chinese National Engineering Research Centre for Tissue Restoration & Reconstruction, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR 999077, China"],"raw_orcid":"https://orcid.org/0000-0002-2470-1077","affiliations":[{"raw_affiliation_string":"Department of Chemistry and the Hong Kong Branch of Chinese National Engineering Research Centre for Tissue Restoration & Reconstruction, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR 999077, China","institution_ids":["https://openalex.org/I200769079"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":["https://openalex.org/A5024502174"],"corresponding_institution_ids":["https://openalex.org/I200769079"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":{"value":4500,"currency":"USD","value_usd":4500},"fwci":2.6816,"has_fulltext":true,"cited_by_count":9,"citation_normalized_percentile":{"value":0.90516312,"is_in_top_1_percent":false,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":96,"max":99},"biblio":{"volume":"147","issue":"27","first_page":"24085","last_page":"24094"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10013","display_name":"Asymmetric Synthesis and Catalysis","score":0.8827999830245972,"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/T10013","display_name":"Asymmetric Synthesis and Catalysis","score":0.8827999830245972,"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/T12251","display_name":"Synthesis and Catalytic Reactions","score":0.05389999970793724,"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":0.01209999993443489,"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/asymmetric-synthesis","display_name":"asymmetric synthesis","score":0.9330000281333923},{"id":"https://openalex.org/keywords/copper-catalysis","display_name":"copper catalysis","score":0.9269999861717224},{"id":"https://openalex.org/keywords/sn2-mechanism","display_name":"SN2 mechanism","score":0.625},{"id":"https://openalex.org/keywords/regioselectivity","display_name":"regioselectivity","score":0.6600000262260437},{"id":"https://openalex.org/keywords/diastereoselectivity","display_name":"diastereoselectivity","score":0.949999988079071},{"id":"https://openalex.org/keywords/strained-heterocycles","display_name":"strained heterocycles","score":0.7210000157356262},{"id":"https://openalex.org/keywords/difunctionalization","display_name":"difunctionalization","score":0.7820000052452087}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9788796305656433},{"id":"https://openalex.org/C146686406","wikidata":"https://www.wikidata.org/wiki/Q898628","display_name":"Enantioselective synthesis","level":3,"score":0.7821541428565979},{"id":"https://openalex.org/C544778455","wikidata":"https://www.wikidata.org/wiki/Q753","display_name":"Copper","level":2,"score":0.7314302921295166},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.6973996162414551},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.42513716220855713},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.37468433380126953},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.3603314459323883}],"mesh":[],"locations_count":5,"locations":[{"id":"doi:10.1021/jacs.5c07821","doi":"https://doi.org/10.1021/jacs.5c07821","is_oa":true,"landing_page_url":"https://doi.org/10.1021/jacs.5c07821","pdf_url":"https://pubs.acs.org/doi/pdf/10.1021/jacs.5c07821?ref=article_openPDF","source":{"id":"https://openalex.org/S111155417","display_name":"Journal of the American Chemical Society","issn_l":"0002-7863","issn":["0002-7863","1520-5126","1943-2984"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","jufo-3","ki-jl-3","medline","norway-2"],"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","license_id":"https://openalex.org/licenses/cc-by","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of the American Chemical Society","raw_type":"journal-article"},{"id":"pmid:40553580","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/40553580","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":"Journal of the American Chemical Society","raw_type":"Journal Article"},{"id":"pmh:oai:europepmc.org:11062796","doi":null,"is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/12257529","pdf_url":null,"source":{"id":"https://openalex.org/S4306400806","display_name":"Europe PMC (PubMed Central)","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1303153112","host_organization_name":"European Bioinformatics Institute","host_organization_lineage":["https://openalex.org/I1303153112"],"host_organization_lineage_names":[],"type":"repository"},"license":"cc-by","license_id":"https://openalex.org/licenses/cc-by","version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":null,"raw_type":"Text"},{"id":"pmh:oai:pubmedcentral.nih.gov:12257529","doi":null,"is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/12257529","pdf_url":null,"source":{"id":"https://openalex.org/S2764455111","display_name":"PubMed Central","issn_l":null,"issn":null,"is_oa":true,"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":"cc-by","license_id":"https://openalex.org/licenses/cc-by","version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":"J Am Chem Soc","raw_type":"Text"},{"id":"pmh:oai:repository.hkust.edu.hk:1783.1-151728","doi":null,"is_oa":false,"landing_page_url":"http://gateway.isiknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=LinksAMR&SrcApp=PARTNER_APP&DestLinkType=FullRecord&DestApp=WOS&KeyUT=001518553100001","pdf_url":null,"source":{"id":"https://openalex.org/S4306401796","display_name":"Rare & Special e-Zone (The Hong Kong University of Science and Technology)","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I200769079","host_organization_name":"Hong Kong University of Science and Technology","host_organization_lineage":["https://openalex.org/I200769079"],"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":"Article"}],"best_oa_location":{"id":"doi:10.1021/jacs.5c07821","doi":"https://doi.org/10.1021/jacs.5c07821","is_oa":true,"landing_page_url":"https://doi.org/10.1021/jacs.5c07821","pdf_url":"https://pubs.acs.org/doi/pdf/10.1021/jacs.5c07821?ref=article_openPDF","source":{"id":"https://openalex.org/S111155417","display_name":"Journal of the American Chemical Society","issn_l":"0002-7863","issn":["0002-7863","1520-5126","1943-2984"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","jufo-3","ki-jl-3","medline","norway-2"],"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","license_id":"https://openalex.org/licenses/cc-by","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of the American Chemical Society","raw_type":"journal-article"},"sustainable_development_goals":[],"sustainable_development_goals_aurora":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G1162233175","display_name":null,"funder_award_id":"22271242","funder_id":"https://openalex.org/F4320321001","funder_display_name":"National Natural Science Foundation of China"},{"id":"https://openalex.org/G1197872373","display_name":"Organocatalytic Asymmetric Construction of All-Carbon Quaternary Stereocenters in Congested Systems","funder_award_id":"16309722","funder_id":"https://openalex.org/F4320321592","funder_display_name":"Research Grants Council, University Grants Committee"},{"id":"https://openalex.org/G1678791140","display_name":null,"funder_award_id":"C6012-21G","funder_id":"https://openalex.org/F4320321592","funder_display_name":"Research Grants Council, University Grants Committee"},{"id":"https://openalex.org/G1946301079","display_name":"Design of Chiral Catalysts and Organocatlytic Processes for Asymmetric Synthesis","funder_award_id":"16309321","funder_id":"https://openalex.org/F4320321592","funder_display_name":"Research Grants Council, University Grants Committee"},{"id":"https://openalex.org/G2310444018","display_name":"Development of New Strategies for the Asymmetric Synthesis of \u03b1-Chiral Carbonyl Compounds","funder_award_id":"16310924","funder_id":"https://openalex.org/F4320321592","funder_display_name":"Research Grants Council, University Grants Committee"},{"id":"https://openalex.org/G3972486685","display_name":"Chiral Phosphoric Acid-Catalyzed Asymmetric Electrochemical Transformations","funder_award_id":"16304322","funder_id":"https://openalex.org/F4320321592","funder_display_name":"Research Grants Council, University Grants Committee"},{"id":"https://openalex.org/G4138877616","display_name":"Regioselective and Stereoselective Addition of Ynones and Siloxy Alkynes","funder_award_id":"16309023","funder_id":"https://openalex.org/F4320321592","funder_display_name":"Research Grants Council, University Grants Committee"},{"id":"https://openalex.org/G4227328392","display_name":null,"funder_award_id":"CNERC14SC01","funder_id":"https://openalex.org/F4320321920","funder_display_name":"Innovation and Technology Commission"},{"id":"https://openalex.org/G534716927","display_name":null,"funder_award_id":"ITC- CNERC-14SC01","funder_id":"https://openalex.org/F4320321920","funder_display_name":"Innovation and Technology Commission"},{"id":"https://openalex.org/G637631384","display_name":null,"funder_award_id":"22471232","funder_id":"https://openalex.org/F4320321001","funder_display_name":"National Natural Science Foundation of China"}],"funders":[{"id":"https://openalex.org/F4320321001","display_name":"National Natural Science Foundation of China","ror":"https://ror.org/01h0zpd94"},{"id":"https://openalex.org/F4320321592","display_name":"Research Grants Council, University Grants Committee","ror":"https://ror.org/00djwmt25"},{"id":"https://openalex.org/F4320321920","display_name":"Innovation and Technology Commission","ror":"https://ror.org/04vf9tr09"},{"id":"https://openalex.org/F4320323539","display_name":"Ministry of Human Resources and Social Security","ror":"https://ror.org/01kjwqy11"}],"has_content":{"grobid_xml":true,"pdf":true},"content_urls":{"pdf":"https://content.openalex.org/works/W4411583582.pdf","grobid_xml":"https://content.openalex.org/works/W4411583582.grobid-xml"},"referenced_works_count":82,"referenced_works":["https://openalex.org/W1966971875","https://openalex.org/W1974431823","https://openalex.org/W1981323957","https://openalex.org/W2009277272","https://openalex.org/W2048439122","https://openalex.org/W2082453673","https://openalex.org/W2100404147","https://openalex.org/W2104499351","https://openalex.org/W2122010784","https://openalex.org/W2127878413","https://openalex.org/W2312672944","https://openalex.org/W2315411185","https://openalex.org/W2328383834","https://openalex.org/W2331824487","https://openalex.org/W2334554189","https://openalex.org/W2407040666","https://openalex.org/W2421771515","https://openalex.org/W2503189821","https://openalex.org/W2504748226","https://openalex.org/W2514118064","https://openalex.org/W2524062342","https://openalex.org/W2531305073","https://openalex.org/W2735665253","https://openalex.org/W2736290476","https://openalex.org/W2737521323","https://openalex.org/W2756503830","https://openalex.org/W2761043211","https://openalex.org/W2761980264","https://openalex.org/W2766631857","https://openalex.org/W2792927639","https://openalex.org/W2804576400","https://openalex.org/W2891820494","https://openalex.org/W2919963083","https://openalex.org/W2944198837","https://openalex.org/W2952576223","https://openalex.org/W2952844095","https://openalex.org/W2953023029","https://openalex.org/W2955542922","https://openalex.org/W2971550740","https://openalex.org/W2990289909","https://openalex.org/W2991143689","https://openalex.org/W2992118066","https://openalex.org/W2996027280","https://openalex.org/W2998935809","https://openalex.org/W3009175817","https://openalex.org/W3064231995","https://openalex.org/W3081375544","https://openalex.org/W3083789601","https://openalex.org/W3093391012","https://openalex.org/W3104101533","https://openalex.org/W3106503857","https://openalex.org/W3112064743","https://openalex.org/W3115627231","https://openalex.org/W3120513725","https://openalex.org/W3137916538","https://openalex.org/W3142304190","https://openalex.org/W3146670653","https://openalex.org/W3201793335","https://openalex.org/W4221007155","https://openalex.org/W4238284361","https://openalex.org/W4254791068","https://openalex.org/W4283161363","https://openalex.org/W4286016594","https://openalex.org/W4297519262","https://openalex.org/W4306409137","https://openalex.org/W4307430227","https://openalex.org/W4308686988","https://openalex.org/W4310946618","https://openalex.org/W4378529411","https://openalex.org/W4385897699","https://openalex.org/W4391246613","https://openalex.org/W4391246739","https://openalex.org/W4392500908","https://openalex.org/W4393249977","https://openalex.org/W4400581728","https://openalex.org/W4401585950","https://openalex.org/W4402981158","https://openalex.org/W4404514318","https://openalex.org/W4405303779","https://openalex.org/W4406494043","https://openalex.org/W4406688521","https://openalex.org/W4411223915"],"related_works":["https://openalex.org/W4391375266","https://openalex.org/W4206261876","https://openalex.org/W3155189705","https://openalex.org/W2118332265","https://openalex.org/W2952040026","https://openalex.org/W2949633962","https://openalex.org/W4206608877","https://openalex.org/W2086778627","https://openalex.org/W4383065574","https://openalex.org/W2507291698"],"abstract_inverted_index":{"High":[0],"Resolution":[1],"Image":[2],"Download":[3],"MS":[4],"PowerPoint":[5],"Slide":[6],"Disclosed":[7],"here":[8],"is":[9],"a":[10,23,35,57,174],"highly":[11],"enantioselective":[12],"difunctionalization":[13],"of":[14,25,50,60,65,76,88,151,178],"azetines":[15],"for":[16,148],"convenient":[17],"access":[18],"to":[19,83,97,154],"chiral":[20,157],"2,3-disubstituted":[21],"azetidines,":[22],"family":[24],"important":[26],"scaffolds":[27],"previously":[28,159],"lacking":[29,160],"general":[30],"access.":[31,162],"With":[32],"Cu/bisphosphine":[33],"as":[34,121,123],"catalyst,":[36],"two":[37,51],"versatile":[38,142],"functionalities":[39,146],"(boryl":[40],"and":[41,68,115,139,144,165],"allyl)":[42],"were":[43,109],"installed":[44],"on":[45,117,126],"azetine":[46,179],"with":[47,111],"concomitant":[48],"construction":[49],"new":[52],"stereogenic":[53],"centers.":[54],"This":[55],"represents":[56],"rare":[58],"demonstration":[59],"Cu-catalyzed":[61],"asymmetric":[62],"boryl":[63,143,176],"alkylation":[64,94],"electron-rich":[66],"olefins":[67],"C\u2550C":[69],"bonds":[70],"in":[71,103],"strained":[72],"heterocycles.":[73],"The":[74,131,141],"use":[75],"allyl":[77,145],"phosphates":[78],"proved":[79],"critical":[80],"not":[81],"only":[82],"overcome":[84],"the":[85,89,118,127,152,170],"low":[86],"reactivity":[87],"borylated":[90],"alkylcuprate":[91],"intermediate":[92],"toward":[93],"but":[95],"also":[96],"avoid":[98],"competing":[99],"side":[100],"reactions.":[101],"Remarkably,":[102],"almost":[104],"all":[105],"cases,":[106],"single":[107],"isomers":[108],"obtained":[110],"complete":[112],"regio-,":[113],"enantio-,":[114],"diastereoselectivies":[116],"azetidine":[119],"motif":[120],"well":[122],"excellent":[124],"control":[125],"double":[128],"bond":[129],"configuration.":[130],"mild":[132],"conditions":[133],"exhibited":[134],"outstanding":[135],"functional":[136],"group":[137],"compatibility":[138],"chemoselectivity.":[140],"allowed":[147],"easy":[149],"transformations":[150],"products":[153],"other":[155],"useful":[156],"azetidines":[158],"straightforward":[161],"Control":[163],"experiments":[164],"kinetic":[166],"studies":[167],"indicated":[168],"that":[169],"reaction":[171],"proceeds":[172],"by":[173,181],"fast":[175],"cupration":[177],"followed":[180],"rate-determining":[182],"allylation":[183],"via":[184],"an":[185],"intrinsically":[186],"controlled":[187],"S":[188],"N":[189],"2\u2032":[190],"pathway.":[191]},"counts_by_year":[{"year":2026,"cited_by_count":6},{"year":2025,"cited_by_count":3}],"updated_date":"2026-09-24T07:57:37.273135","created_date":"2025-10-10T00:00:00"}