{"id":"https://openalex.org/W2006448313","doi":"https://doi.org/10.1021/ja8097349","title":"Phosphine-Promoted [3 + 3] Annulations of Aziridines With Allenoates: Facile Entry Into Highly Functionalized Tetrahydropyridines","display_name":"Phosphine-Promoted [3 + 3] Annulations of Aziridines With Allenoates: Facile Entry Into Highly Functionalized Tetrahydropyridines","publication_year":2009,"publication_date":"2009-04-17","ids":{"openalex":"https://openalex.org/W2006448313","doi":"https://doi.org/10.1021/ja8097349","mag":"2006448313","pmid":"https://pubmed.ncbi.nlm.nih.gov/19374356","pmcid":"https://www.ncbi.nlm.nih.gov/pmc/articles/2749062"},"language":"en","primary_location":{"id":"doi:10.1021/ja8097349","doi":"https://doi.org/10.1021/ja8097349","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja8097349","pdf_url":null,"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","dongbi-a","jufo-3","ki-jl-3","medline","norway-2","poland-200","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":"Journal of the American Chemical Society","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":"https://www.ncbi.nlm.nih.gov/pmc/articles/2749062","any_repository_has_fulltext":true},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5091836844","display_name":"Hongchao Guo","orcid":"https://orcid.org/0000-0002-7356-4283","observed_orcids":["https://orcid.org/0000-0002-7356-4283","https://orcid.org/0009-0007-0413-0354"]},"institutions":[{"id":"https://openalex.org/I161318765","display_name":"University of California, Los Angeles","ror":"https://ror.org/046rm7j60","country_code":"US","type":"education","lineage":["https://openalex.org/I161318765"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Hongchao Guo","raw_affiliation_strings":["Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569","Department of Chemistry & Biochemistry, University of California, Los Angeles, California 90095-1569, USA"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569","institution_ids":["https://openalex.org/I161318765"]},{"raw_affiliation_string":"Department of Chemistry & Biochemistry, University of California, Los Angeles, California 90095-1569, USA","institution_ids":["https://openalex.org/I161318765"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5100826171","display_name":"Qihai Xu","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I161318765","display_name":"University of California, Los Angeles","ror":"https://ror.org/046rm7j60","country_code":"US","type":"education","lineage":["https://openalex.org/I161318765"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Qihai Xu","raw_affiliation_strings":["Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569","institution_ids":["https://openalex.org/I161318765"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5039075754","display_name":"Ohyun Kwon","orcid":"https://orcid.org/0000-0002-5405-3971","observed_orcids":["https://orcid.org/0000-0002-5405-3971"]},"institutions":[{"id":"https://openalex.org/I161318765","display_name":"University of California, Los Angeles","ror":"https://ror.org/046rm7j60","country_code":"US","type":"education","lineage":["https://openalex.org/I161318765"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"Ohyun Kwon","raw_affiliation_strings":["Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569","institution_ids":["https://openalex.org/I161318765"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":["https://openalex.org/A5039075754"],"corresponding_institution_ids":["https://openalex.org/I161318765"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":10.4178,"has_fulltext":false,"cited_by_count":203,"citation_normalized_percentile":{"value":0.99211026,"is_in_top_1_percent":true,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":89,"max":100},"biblio":{"volume":"131","issue":"18","first_page":"6318","last_page":"6319"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T12251","display_name":"Synthesis and Catalytic Reactions","score":0.3434999883174896,"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/T12251","display_name":"Synthesis and Catalytic Reactions","score":0.3434999883174896,"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/T13239","display_name":"Phosphorus compounds and reactions","score":0.24709999561309814,"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/T10013","display_name":"Asymmetric Synthesis and Catalysis","score":0.09510000050067902,"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/phosphine-catalysis","display_name":"phosphine catalysis","score":0.781000018119812},{"id":"https://openalex.org/keywords/3-3-annulation","display_name":"[3+3] annulation","score":0.8840000033378601},{"id":"https://openalex.org/keywords/aziridines","display_name":"aziridines","score":0.996999979019165},{"id":"https://openalex.org/keywords/allenoates","display_name":"allenoates","score":0.9860000014305115},{"id":"https://openalex.org/keywords/tetrahydropyridines","display_name":"tetrahydropyridines","score":0.9819999933242798},{"id":"https://openalex.org/keywords/nucleophilic-aromatic-substitution","display_name":"nucleophilic aromatic substitution","score":0.8330000042915344},{"id":"https://openalex.org/keywords/desulfonylation","display_name":"desulfonylation","score":0.9620000123977661},{"id":"https://openalex.org/keywords/cycloaddition-mechanism","display_name":"cycloaddition mechanism","score":0.7250000238418579},{"id":"https://openalex.org/keywords/e-z-selectivity","display_name":"E/Z selectivity","score":0.7549999952316284},{"id":"https://openalex.org/keywords/allenes","display_name":"allenes","score":0.4090000092983246}],"concepts":[{"id":"https://openalex.org/C2777716191","wikidata":"https://www.wikidata.org/wiki/Q207877","display_name":"Phosphine","level":3,"score":0.9724057912826538},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.928568959236145},{"id":"https://openalex.org/C178907741","wikidata":"https://www.wikidata.org/wiki/Q745930","display_name":"Nucleophile","level":3,"score":0.8054460883140564},{"id":"https://openalex.org/C2779664164","wikidata":"https://www.wikidata.org/wiki/Q898648","display_name":"Cycloaddition","level":3,"score":0.5908815860748291},{"id":"https://openalex.org/C135731615","wikidata":"https://www.wikidata.org/wiki/Q658656","display_name":"Nucleophilic substitution","level":2,"score":0.5502066612243652},{"id":"https://openalex.org/C9061509","wikidata":"https://www.wikidata.org/wiki/Q901713","display_name":"Nucleophilic aromatic substitution","level":3,"score":0.46731847524642944},{"id":"https://openalex.org/C20774148","wikidata":"https://www.wikidata.org/wiki/Q901669","display_name":"Nucleophilic addition","level":3,"score":0.4340084195137024},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.43012210726737976},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.4054121971130371},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.3881438970565796},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.35623297095298767}],"mesh":[{"descriptor_ui":"D000466","descriptor_name":"Alkadienes","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D001388","descriptor_name":"Aziridines","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D002264","descriptor_name":"Carboxylic Acids","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D002384","descriptor_name":"Catalysis","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D010720","descriptor_name":"Phosphines","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D011725","descriptor_name":"Pyridines","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true}],"locations_count":4,"locations":[{"id":"doi:10.1021/ja8097349","doi":"https://doi.org/10.1021/ja8097349","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja8097349","pdf_url":null,"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","dongbi-a","jufo-3","ki-jl-3","medline","norway-2","poland-200","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":"Journal of the American Chemical Society","raw_type":"journal-article"},{"id":"pmid:19374356","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/19374356","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:1967238","doi":null,"is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/2749062","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":null,"license_id":null,"version":"acceptedVersion","is_accepted":true,"is_published":false,"raw_source_name":null,"raw_type":"Text"},{"id":"pmh:oai:pubmedcentral.nih.gov:2749062","doi":null,"is_oa":true,"landing_page_url":"https://pmc.ncbi.nlm.nih.gov/articles/PMC2749062/","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":null,"license_id":null,"version":"acceptedVersion","is_accepted":true,"is_published":false,"raw_source_name":"J Am Chem Soc","raw_type":"Text"}],"best_oa_location":{"id":"pmh:oai:europepmc.org:1967238","doi":null,"is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/2749062","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":null,"license_id":null,"version":"acceptedVersion","is_accepted":true,"is_published":false,"raw_source_name":null,"raw_type":"Text"},"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G5799406652","display_name":"Pilot-Scale Library Production Based on Phosphine Catalysis of Allenes","funder_award_id":"P41GM081282","funder_id":"https://openalex.org/F4320337354","funder_display_name":"National Institute of General Medical Sciences"},{"id":"https://openalex.org/G9000912852","display_name":"Phosphine-Catalyzed Annulations and their Applications","funder_award_id":"R01GM071779","funder_id":"https://openalex.org/F4320337354","funder_display_name":"National Institute of General Medical Sciences"}],"funders":[{"id":"https://openalex.org/F4320337354","display_name":"National Institute of General Medical Sciences","ror":"https://ror.org/04q48ey07"}],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":39,"referenced_works":["https://openalex.org/W1531637720","https://openalex.org/W1969780045","https://openalex.org/W1970511278","https://openalex.org/W1974965866","https://openalex.org/W1977706373","https://openalex.org/W1981899811","https://openalex.org/W1985226187","https://openalex.org/W1986483761","https://openalex.org/W1987635290","https://openalex.org/W1991520288","https://openalex.org/W1993553618","https://openalex.org/W1997217559","https://openalex.org/W2005333450","https://openalex.org/W2017280600","https://openalex.org/W2018930157","https://openalex.org/W2026483723","https://openalex.org/W2027512701","https://openalex.org/W2034266199","https://openalex.org/W2039286055","https://openalex.org/W2054246966","https://openalex.org/W2058161057","https://openalex.org/W2068811226","https://openalex.org/W2083061046","https://openalex.org/W2090569733","https://openalex.org/W2106883606","https://openalex.org/W2111604495","https://openalex.org/W2126313210","https://openalex.org/W2127716830","https://openalex.org/W2145246173","https://openalex.org/W2146070037","https://openalex.org/W2172290731","https://openalex.org/W2322188824","https://openalex.org/W2606647631","https://openalex.org/W2915298571","https://openalex.org/W2949545996","https://openalex.org/W2949890744","https://openalex.org/W2950252422","https://openalex.org/W2950311249","https://openalex.org/W2950973057"],"related_works":["https://openalex.org/W2949079738","https://openalex.org/W2910840769","https://openalex.org/W2749179640","https://openalex.org/W3143591968","https://openalex.org/W2027633785","https://openalex.org/W4393158835","https://openalex.org/W3107432666","https://openalex.org/W2161041169","https://openalex.org/W2167579499","https://openalex.org/W2014726290"],"abstract_inverted_index":{"The":[0],"phosphine-mediated":[1],"[3":[2],"+":[3],"3]":[4],"annulations":[5],"of":[6,22,28,35,46,50,54,81],"aziridines":[7,82],"and":[8,32,63],"allenes":[9],"are":[10,44,76],"experimentally":[11],"simple":[12],"reactions,":[13],"run":[14],"under":[15],"very":[16],"mild":[17],"conditions,":[18],"for":[19],"the":[20,52,77],"preparation":[21],"highly":[23],"functionalized":[24],"tetrahydropyridines":[25],"in":[26,86],"yields":[27],"up":[29,36],"to":[30,37,41],"98%":[31],"trans/cis":[33],"ratios":[34],"97:3.":[38],"In":[39],"addition":[40],"steps":[42],"that":[43],"typical":[45],"nucleophilic":[47,60,87],"phosphine-catalyzed":[48,88],"reactions":[49,75],"allenoates,":[51],"mechanism":[53],"this":[55],"new":[56],"reaction":[57,84],"features":[58],"apparent":[59],"aromatic":[61],"substitution":[62],"concomitant":[64],"desulfonylation,":[65],"processes":[66],"hitherto":[67],"unknown":[68],"during":[69],"phosphine-promoted":[70],"cycloaddition":[71],"reactions.":[72],"Notably,":[73],"these":[74],"first":[78],"reported":[79],"examples":[80],"as":[83],"partners":[85],"transformations.":[89]},"counts_by_year":[{"year":2026,"cited_by_count":3},{"year":2025,"cited_by_count":1},{"year":2024,"cited_by_count":3},{"year":2023,"cited_by_count":5},{"year":2022,"cited_by_count":7},{"year":2021,"cited_by_count":4},{"year":2020,"cited_by_count":8},{"year":2019,"cited_by_count":13},{"year":2018,"cited_by_count":14},{"year":2017,"cited_by_count":16},{"year":2016,"cited_by_count":18},{"year":2015,"cited_by_count":12},{"year":2014,"cited_by_count":15},{"year":2013,"cited_by_count":14},{"year":2012,"cited_by_count":22}],"updated_date":"2026-11-12T12:28:57.059296","created_date":"2016-06-24T00:00:00"}
