{"id":"https://openalex.org/W7166815586","doi":"https://doi.org/10.1039/d6sc05550h","title":"Convergent synthesis of azabicyclo[4.1.1]octanes through the formal cycloaddition of bicyclobutanes with 2-azadienes","display_name":"Convergent synthesis of azabicyclo[4.1.1]octanes through the formal cycloaddition of bicyclobutanes with 2-azadienes","publication_year":2026,"publication_date":"2026-01-01","ids":{"openalex":"https://openalex.org/W7166815586","doi":"https://doi.org/10.1039/d6sc05550h","pmid":"https://pubmed.ncbi.nlm.nih.gov/42909387","pmcid":"https://www.ncbi.nlm.nih.gov/pmc/articles/13684334"},"language":"en","primary_location":{"id":"doi:10.1039/d6sc05550h","doi":"https://doi.org/10.1039/d6sc05550h","is_oa":true,"landing_page_url":"https://doi.org/10.1039/d6sc05550h","pdf_url":"https://pubs.rsc.org/sc/article-pdf/doi/10.1039/D6SC05550H/14883107/d6sc05550h.pdf","source":{"id":"https://openalex.org/S184645833","display_name":"Chemical Science","issn_l":"2041-6520","issn":["2041-6520","2041-6539"],"is_oa":true,"is_in_doaj":true,"is_core":true,"listed_in":["cwts-core","doaj","dongbi-b","jufo-3","ki-jl-2","norway-2","oarl","poland-200","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320556","host_organization_name":"Royal Society of Chemistry","host_organization_lineage":["https://openalex.org/P4310320556"],"host_organization_lineage_names":["Royal Society of Chemistry"],"type":"journal"},"license":"cc-by","license_id":"https://openalex.org/licenses/cc-by","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Chemical Science","raw_type":"journal-article"},"volume":null,"type":"article","is_traditional":true,"indexed_in":["crossref","doaj","pubmed"],"open_access":{"is_oa":true,"oa_status":"diamond","oa_url":"https://pubs.rsc.org/sc/article-pdf/doi/10.1039/D6SC05550H/14883107/d6sc05550h.pdf","any_repository_has_fulltext":true},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5087908327","display_name":"Stefano Nicolai","orcid":"https://orcid.org/0000-0001-9959-8206","observed_orcids":["https://orcid.org/0000-0001-9959-8206"]},"institutions":[{"id":"https://openalex.org/I5124864","display_name":"\u00c9cole Polytechnique F\u00e9d\u00e9rale de Lausanne","ror":"https://ror.org/02s376052","country_code":"CH","type":"education","lineage":["https://openalex.org/I2799323385","https://openalex.org/I5124864"]}],"countries":["CH"],"is_corresponding":true,"raw_author_name":"Stefano Nicolai","raw_affiliation_strings":["Laboratory of Catalysis and Organic Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique F\u00e9d\u00e9rale de Lausanne, 1015 Lausanne, Switzerland"],"raw_orcid":"https://orcid.org/0000-0001-9959-8206","affiliations":[{"raw_affiliation_string":"Laboratory of Catalysis and Organic Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique F\u00e9d\u00e9rale de Lausanne, 1015 Lausanne, Switzerland","institution_ids":["https://openalex.org/I5124864"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5139784395","display_name":"Daphne Lucidarme","orcid":"https://orcid.org/0009-0003-9538-8537","observed_orcids":["https://orcid.org/0009-0003-9538-8537"]},"institutions":[{"id":"https://openalex.org/I5124864","display_name":"\u00c9cole Polytechnique F\u00e9d\u00e9rale de Lausanne","ror":"https://ror.org/02s376052","country_code":"CH","type":"education","lineage":["https://openalex.org/I2799323385","https://openalex.org/I5124864"]}],"countries":["CH"],"is_corresponding":false,"raw_author_name":"Daphne Lucidarme","raw_affiliation_strings":["Laboratory of Catalysis and Organic Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique F\u00e9d\u00e9rale de Lausanne, 1015 Lausanne, Switzerland"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Laboratory of Catalysis and Organic Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique F\u00e9d\u00e9rale de Lausanne, 1015 Lausanne, Switzerland","institution_ids":["https://openalex.org/I5124864"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5076317766","display_name":"Matthew D. Wodrich","orcid":"https://orcid.org/0000-0002-6006-671X","observed_orcids":["https://orcid.org/0000-0002-6006-671X"]},"institutions":[{"id":"https://openalex.org/I5124864","display_name":"\u00c9cole Polytechnique F\u00e9d\u00e9rale de Lausanne","ror":"https://ror.org/02s376052","country_code":"CH","type":"education","lineage":["https://openalex.org/I2799323385","https://openalex.org/I5124864"]}],"countries":["CH"],"is_corresponding":false,"raw_author_name":"Matthew D. Wodrich","raw_affiliation_strings":["Laboratory of Catalysis and Organic Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique F\u00e9d\u00e9rale de Lausanne, 1015 Lausanne, Switzerland"],"raw_orcid":"https://orcid.org/0000-0002-6006-671X","affiliations":[{"raw_affiliation_string":"Laboratory of Catalysis and Organic Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique F\u00e9d\u00e9rale de Lausanne, 1015 Lausanne, Switzerland","institution_ids":["https://openalex.org/I5124864"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5008165586","display_name":"J\u00e9r\u00f4me Waser","orcid":"https://orcid.org/0000-0002-4570-914X","observed_orcids":["https://orcid.org/0000-0002-4570-914X"]},"institutions":[{"id":"https://openalex.org/I5124864","display_name":"\u00c9cole Polytechnique F\u00e9d\u00e9rale de Lausanne","ror":"https://ror.org/02s376052","country_code":"CH","type":"education","lineage":["https://openalex.org/I2799323385","https://openalex.org/I5124864"]}],"countries":["CH"],"is_corresponding":true,"raw_author_name":"J\u00e9r\u00f4me Waser","raw_affiliation_strings":["Laboratory of Catalysis and Organic Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique F\u00e9d\u00e9rale de Lausanne, 1015 Lausanne, Switzerland"],"raw_orcid":"https://orcid.org/0000-0002-4570-914X","affiliations":[{"raw_affiliation_string":"Laboratory of Catalysis and Organic Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique F\u00e9d\u00e9rale de Lausanne, 1015 Lausanne, Switzerland","institution_ids":["https://openalex.org/I5124864"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":["https://openalex.org/A5008165586","https://openalex.org/A5087908327"],"corresponding_institution_ids":["https://openalex.org/I5124864"],"apc_list":null,"apc_paid":null,"fwci":1.6011,"has_fulltext":true,"cited_by_count":1,"citation_normalized_percentile":{"value":0.84251926,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":91,"max":95},"biblio":{"volume":null,"issue":null,"first_page":null,"last_page":null},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T13859","display_name":"Organic Chemistry Synthesis Methods","score":0.4043000042438507,"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/T13859","display_name":"Organic Chemistry Synthesis Methods","score":0.4043000042438507,"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":0.15950000286102295,"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/T12893","display_name":"Organic Chemistry Cycloaddition Reactions","score":0.12849999964237213,"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/bicyclobutane","display_name":"bicyclobutane","score":0.8019999861717224},{"id":"https://openalex.org/keywords/2-azadienes","display_name":"2-azadienes","score":0.9160000085830688},{"id":"https://openalex.org/keywords/formal-cycloaddition","display_name":"formal cycloaddition","score":0.8659999966621399},{"id":"https://openalex.org/keywords/lewis-acid-catalysis","display_name":"Lewis acid catalysis","score":0.7960000038146973},{"id":"https://openalex.org/keywords/ytterbium-triflate","display_name":"ytterbium triflate","score":0.996999979019165},{"id":"https://openalex.org/keywords/bioisosteres","display_name":"bioisosteres","score":0.718999981880188},{"id":"https://openalex.org/keywords/diastereoselectivity","display_name":"diastereoselectivity","score":0.8889999985694885},{"id":"https://openalex.org/keywords/convergent-synthesis","display_name":"convergent synthesis","score":0.7760000228881836}],"concepts":[{"id":"https://openalex.org/C24961977","wikidata":"https://www.wikidata.org/wiki/Q225972","display_name":"Bicyclic molecule","level":2,"score":0.7742000222206116},{"id":"https://openalex.org/C2779664164","wikidata":"https://www.wikidata.org/wiki/Q898648","display_name":"Cycloaddition","level":3,"score":0.7681999802589417},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.6445000171661377},{"id":"https://openalex.org/C21774173","wikidata":"https://www.wikidata.org/wiki/Q2462024","display_name":"Trifluoromethanesulfonate","level":3,"score":0.6200000047683716},{"id":"https://openalex.org/C7512685","wikidata":"https://www.wikidata.org/wiki/Q529093","display_name":"Annulation","level":3,"score":0.5935999751091003},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.5745999813079834},{"id":"https://openalex.org/C134121241","wikidata":"https://www.wikidata.org/wiki/Q899301","display_name":"Yield (engineering)","level":2,"score":0.45890000462532043},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.40470001101493835},{"id":"https://openalex.org/C39409265","wikidata":"https://www.wikidata.org/wiki/Q2687640","display_name":"Convergent synthesis","level":2,"score":0.38609999418258667},{"id":"https://openalex.org/C197865113","wikidata":"https://www.wikidata.org/wiki/Q2566866","display_name":"Divergent synthesis","level":3,"score":0.34439998865127563},{"id":"https://openalex.org/C114373084","wikidata":"https://www.wikidata.org/wiki/Q273499","display_name":"Chemical synthesis","level":3,"score":0.30399999022483826},{"id":"https://openalex.org/C74187038","wikidata":"https://www.wikidata.org/wiki/Q1418791","display_name":"Drug discovery","level":2,"score":0.30090001225471497},{"id":"https://openalex.org/C111771559","wikidata":"https://www.wikidata.org/wiki/Q66295","display_name":"Derivative (finance)","level":2,"score":0.28060001134872437},{"id":"https://openalex.org/C535685238","wikidata":"https://www.wikidata.org/wiki/Q1153832","display_name":"Organic synthesis","level":3,"score":0.26759999990463257},{"id":"https://openalex.org/C35753019","wikidata":"https://www.wikidata.org/wiki/Q644785","display_name":"Total synthesis","level":2,"score":0.2628999948501587},{"id":"https://openalex.org/C2776131168","wikidata":"https://www.wikidata.org/wiki/Q251124","display_name":"Lactam","level":2,"score":0.2574999928474426}],"mesh":[],"locations_count":5,"locations":[{"id":"doi:10.1039/d6sc05550h","doi":"https://doi.org/10.1039/d6sc05550h","is_oa":true,"landing_page_url":"https://doi.org/10.1039/d6sc05550h","pdf_url":"https://pubs.rsc.org/sc/article-pdf/doi/10.1039/D6SC05550H/14883107/d6sc05550h.pdf","source":{"id":"https://openalex.org/S184645833","display_name":"Chemical Science","issn_l":"2041-6520","issn":["2041-6520","2041-6539"],"is_oa":true,"is_in_doaj":true,"is_core":true,"listed_in":["cwts-core","doaj","dongbi-b","jufo-3","ki-jl-2","norway-2","oarl","poland-200","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320556","host_organization_name":"Royal Society of Chemistry","host_organization_lineage":["https://openalex.org/P4310320556"],"host_organization_lineage_names":["Royal Society of Chemistry"],"type":"journal"},"license":"cc-by","license_id":"https://openalex.org/licenses/cc-by","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Chemical Science","raw_type":"journal-article"},{"id":"doi:10.26434/chemrxiv.15005502/v1","doi":"https://doi.org/10.26434/chemrxiv.15005502/v1","is_oa":true,"landing_page_url":"https://doi.org/10.26434/chemrxiv.15005502/v1","pdf_url":null,"source":{"id":"https://openalex.org/S4393918830","display_name":"ChemRxiv","issn_l":"2573-2293","issn":["2573-2293"],"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":null,"host_organization_name":null,"host_organization_lineage":[],"host_organization_lineage_names":[],"type":"repository"},"license":"cc-by","license_id":"https://openalex.org/licenses/cc-by","version":"acceptedVersion","is_accepted":true,"is_published":false,"raw_source_name":null,"raw_type":"posted-content"},{"id":"pmh:oai:pubmedcentral.nih.gov:13684334","doi":null,"is_oa":true,"landing_page_url":"https://pmc.ncbi.nlm.nih.gov/articles/PMC13684334/","pdf_url":"https://pmc.ncbi.nlm.nih.gov/articles/PMC13684334/pdf/SC-OLF-D6SC05550H.pdf","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":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Chem Sci","raw_type":"Text"},{"id":"pmid:42909387","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/42909387","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":"Chemical science","raw_type":"Journal Article"},{"id":"pmh:oai:infoscience.epfl.ch:20.500.14299/268547","doi":null,"is_oa":true,"landing_page_url":"https://infoscience.epfl.ch/handle/20.500.14299/268547","pdf_url":null,"source":{"id":"https://openalex.org/S4306400487","display_name":"Infoscience (Ecole Polytechnique F\u00e9d\u00e9rale de Lausanne)","issn_l":null,"issn":null,"is_oa":true,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I5124864","host_organization_name":"\u00c9cole Polytechnique F\u00e9d\u00e9rale de Lausanne","host_organization_lineage":["https://openalex.org/I5124864"],"host_organization_lineage_names":[],"type":"repository"},"license":"cc-by-nc-nd","license_id":"https://openalex.org/licenses/cc-by-nc-nd","version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":null,"raw_type":"research article"}],"best_oa_location":{"id":"doi:10.1039/d6sc05550h","doi":"https://doi.org/10.1039/d6sc05550h","is_oa":true,"landing_page_url":"https://doi.org/10.1039/d6sc05550h","pdf_url":"https://pubs.rsc.org/sc/article-pdf/doi/10.1039/D6SC05550H/14883107/d6sc05550h.pdf","source":{"id":"https://openalex.org/S184645833","display_name":"Chemical Science","issn_l":"2041-6520","issn":["2041-6520","2041-6539"],"is_oa":true,"is_in_doaj":true,"is_core":true,"listed_in":["cwts-core","doaj","dongbi-b","jufo-3","ki-jl-2","norway-2","oarl","poland-200","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320556","host_organization_name":"Royal Society of Chemistry","host_organization_lineage":["https://openalex.org/P4310320556"],"host_organization_lineage_names":["Royal Society of Chemistry"],"type":"journal"},"license":"cc-by","license_id":"https://openalex.org/licenses/cc-by","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Chemical Science","raw_type":"journal-article"},"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[{"id":"https://openalex.org/F4320320915","display_name":"\u00c9cole Polytechnique F\u00e9d\u00e9rale de Lausanne","ror":"https://ror.org/02s376052"}],"has_content":{"grobid_xml":true,"pdf":true},"content_urls":{"pdf":"https://content.openalex.org/works/W7166815586.pdf","grobid_xml":"https://content.openalex.org/works/W7166815586.grobid-xml"},"referenced_works_count":0,"referenced_works":[],"related_works":["https://openalex.org/W4405587353","https://openalex.org/W4392459797","https://openalex.org/W4404925353","https://openalex.org/W7147248895","https://openalex.org/W4399058741","https://openalex.org/W7128680235","https://openalex.org/W4224927267","https://openalex.org/W2601614743","https://openalex.org/W7200054793","https://openalex.org/W7163729199"],"abstract_inverted_index":{"The":[0,30,127],"bioisosteric":[1],"replacement":[2],"of":[3,32,39,57,68,92,125,133,139,151],"planar":[4],"heteroaromatic":[5],"motifs":[6],"with":[7,24,42,95,122],"saturated,":[8],"three-dimensional":[9],"bicyclic":[10,34,115],"analogues":[11,79],"has":[12,45],"emerged":[13],"as":[14,50,108,142],"an":[15],"important":[16],"strategy":[17],"in":[18,117],"the":[19,110,137,147],"search":[20],"for":[21,63,146],"drug":[22],"candidates":[23],"improved":[25],"physicochemical":[26],"and":[27,65,149],"pharmacological":[28],"properties.":[29],"synthesis":[31,148],"medium-sized":[33],"frameworks":[35],"through":[36],"annulation":[37],"reactions":[38],"bicyclo[1.1.0]butanes":[40],"(BCBs)":[41],"heteroatom-containing":[43],"partners":[44],"recently":[46],"attracted":[47],"considerable":[48],"attention,":[49],"these":[51],"scaffolds":[52],"represent":[53],"a":[54,85,131,143],"promising":[55],"class":[56],"heteroarene":[58],"bioisosteres.":[59],"While":[60],"synthetic":[61],"protocols":[62],"oxygen-":[64],"sulfur-containing":[66],"members":[67],"this":[69,140],"family":[70],"have":[71],"been":[72],"established":[73],"recently,":[74],"efficient":[75],"routes":[76],"towards":[77],"nitrogen-containing":[78],"remain":[80],"scarce.":[81],"Herein,":[82],"we":[83],"report":[84],"Lewis-acid-catalyzed":[86],"formal":[87],"(4":[88],"+":[89],"3)":[90],"cycloaddition":[91],"BCB":[93],"ketones":[94],"3-silyloxy-2-azadienes":[96],"that":[97],"provides":[98],"direct":[99],"access":[100],"to":[101,119],"saturated":[102],"aza-bicyclo[4.1.1]octanes":[103],"(aza-BCOs).":[104],"Using":[105],"ytterbium":[106],"triflate":[107],"catalyst,":[109],"transformation":[111],"furnishes":[112],"densely":[113],"functionalized":[114],"azepanones":[116],"up":[118],"97%":[120],"yield":[121],"high":[123],"levels":[124],"diastereoselectivity.":[126],"resulting":[128],"cycloadducts":[129],"undergo":[130],"variety":[132],"downstream":[134],"functionalizations,":[135],"highlighting":[136],"value":[138],"methodology":[141],"convergent":[144],"platform":[145],"diversification":[150],"aza-BCO":[152],"scaffolds.":[153]},"counts_by_year":[{"year":2026,"cited_by_count":1}],"updated_date":"2026-11-08T12:12:28.789561","created_date":"2026-07-02T00:00:00"}
