{"id":"https://openalex.org/W7225614740","doi":"https://doi.org/10.1021/acs.orglett.6c04045","title":"Ru-Catalyzed Alkene Isomerization Triggers Winstein Rearrangement for Stereoselective Allylic Azide Synthesis","display_name":"Ru-Catalyzed Alkene Isomerization Triggers Winstein Rearrangement for Stereoselective Allylic Azide Synthesis","publication_year":2026,"publication_date":"2026-11-09","ids":{"openalex":"https://openalex.org/W7225614740","doi":"https://doi.org/10.1021/acs.orglett.6c04045"},"language":"en","primary_location":{"id":"doi:10.1021/acs.orglett.6c04045","doi":"https://doi.org/10.1021/acs.orglett.6c04045","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.orglett.6c04045","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"],"open_access":{"is_oa":false,"oa_status":"closed","oa_url":null,"any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5161324358","display_name":"Chun-Han Huang","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I135551196","display_name":"National Kaohsiung Normal University","ror":"https://ror.org/04tsc8g87","country_code":"TW","type":"education","lineage":["https://openalex.org/I135551196"]}],"countries":["TW"],"is_corresponding":false,"raw_author_name":"Chun-Han Huang","raw_affiliation_strings":["National Kaohsiung Normal University , , No. 62, Shenjhong Road, Yanchao District , ,"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"National Kaohsiung Normal University , , No. 62, Shenjhong Road, Yanchao District , ,","institution_ids":["https://openalex.org/I135551196"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5161314755","display_name":"Chia-Hui Chen","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I135551196","display_name":"National Kaohsiung Normal University","ror":"https://ror.org/04tsc8g87","country_code":"TW","type":"education","lineage":["https://openalex.org/I135551196"]}],"countries":["TW"],"is_corresponding":false,"raw_author_name":"Chia-Hui Chen","raw_affiliation_strings":["National Kaohsiung Normal University , , No. 62, Shenjhong Road, Yanchao District , ,"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"National Kaohsiung Normal University , , No. 62, Shenjhong Road, Yanchao District , ,","institution_ids":["https://openalex.org/I135551196"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5080036154","display_name":"Pei-Lin Hsu","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I135551196","display_name":"National Kaohsiung Normal University","ror":"https://ror.org/04tsc8g87","country_code":"TW","type":"education","lineage":["https://openalex.org/I135551196"]}],"countries":["TW"],"is_corresponding":false,"raw_author_name":"Pei-Lin Hsu","raw_affiliation_strings":["National Kaohsiung Normal University , , No. 62, Shenjhong Road, Yanchao District , ,"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"National Kaohsiung Normal University , , No. 62, Shenjhong Road, Yanchao District , ,","institution_ids":["https://openalex.org/I135551196"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5079665365","display_name":"Siang-Ying Chen","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I135551196","display_name":"National Kaohsiung Normal University","ror":"https://ror.org/04tsc8g87","country_code":"TW","type":"education","lineage":["https://openalex.org/I135551196"]}],"countries":["TW"],"is_corresponding":false,"raw_author_name":"Siang-Ying Chen","raw_affiliation_strings":["National Kaohsiung Normal University , , No. 62, Shenjhong Road, Yanchao District , ,"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"National Kaohsiung Normal University , , No. 62, Shenjhong Road, Yanchao District , ,","institution_ids":["https://openalex.org/I135551196"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5161320351","display_name":"Yu-En Tai","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I135551196","display_name":"National Kaohsiung Normal University","ror":"https://ror.org/04tsc8g87","country_code":"TW","type":"education","lineage":["https://openalex.org/I135551196"]}],"countries":["TW"],"is_corresponding":false,"raw_author_name":"Yu-En Tai","raw_affiliation_strings":["National Kaohsiung Normal University , , No. 62, Shenjhong Road, Yanchao District , ,"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"National Kaohsiung Normal University , , No. 62, Shenjhong Road, Yanchao District , ,","institution_ids":["https://openalex.org/I135551196"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5161360680","display_name":"Guan-Wen Lin","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I135551196","display_name":"National Kaohsiung Normal University","ror":"https://ror.org/04tsc8g87","country_code":"TW","type":"education","lineage":["https://openalex.org/I135551196"]}],"countries":["TW"],"is_corresponding":false,"raw_author_name":"Guan-Wen Lin","raw_affiliation_strings":["National Kaohsiung Normal University , , No. 62, Shenjhong Road, Yanchao District , ,"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"National Kaohsiung Normal University , , No. 62, Shenjhong Road, Yanchao District , ,","institution_ids":["https://openalex.org/I135551196"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5001418733","display_name":"Guo\u2010Ming Ho","orcid":"https://orcid.org/0000-0003-0463-9170","observed_orcids":["https://orcid.org/0000-0003-0463-9170"]},"institutions":[{"id":"https://openalex.org/I135551196","display_name":"National Kaohsiung Normal University","ror":"https://ror.org/04tsc8g87","country_code":"TW","type":"education","lineage":["https://openalex.org/I135551196"]}],"countries":["TW"],"is_corresponding":true,"raw_author_name":"Guo-Ming Ho","raw_affiliation_strings":["National Kaohsiung Normal University , , No. 62, Shenjhong Road, Yanchao District , ,"],"raw_orcid":"https://orcid.org/0000-0003-0463-9170","affiliations":[{"raw_affiliation_string":"National Kaohsiung Normal University , , No. 62, Shenjhong Road, Yanchao District , ,","institution_ids":["https://openalex.org/I135551196"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":["https://openalex.org/A5001418733"],"corresponding_institution_ids":["https://openalex.org/I135551196"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":0.0,"has_fulltext":false,"cited_by_count":0,"citation_normalized_percentile":{"value":0.0,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":null,"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/T10013","display_name":"Asymmetric Synthesis and Catalysis","score":0.42719998955726624,"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":0.42719998955726624,"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/T11611","display_name":"Cyclopropane Reaction Mechanisms","score":0.20280000567436218,"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":0.10779999941587448,"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":0.9330000281333923},{"id":"https://openalex.org/keywords/alkene-isomerization","display_name":"olefin isomerization","score":0.9959999918937683},{"id":"https://openalex.org/keywords/3-3-sigmatropic-rearrangement","display_name":"[3,3]-sigmatropic rearrangement","score":0.9070000052452087},{"id":"https://openalex.org/keywords/allylic-azides","display_name":"allylic azides","score":0.8299999833106995},{"id":"https://openalex.org/keywords/stereoselective-synthesis","display_name":"stereoselective synthesis","score":0.8600000143051147},{"id":"https://openalex.org/keywords/enantiomeric-purity","display_name":"enantiomeric purity","score":0.6690000295639038},{"id":"https://openalex.org/keywords/cascade-reactions","display_name":"cascade reactions","score":0.5870000123977661},{"id":"https://openalex.org/keywords/one-pot-synthesis","display_name":"one-pot synthesis","score":0.6930000185966492}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9395999908447266},{"id":"https://openalex.org/C2776254738","wikidata":"https://www.wikidata.org/wiki/Q81406","display_name":"Alkene","level":3,"score":0.8682000041007996},{"id":"https://openalex.org/C126661725","wikidata":"https://www.wikidata.org/wiki/Q903420","display_name":"Isomerization","level":3,"score":0.8629999756813049},{"id":"https://openalex.org/C120095180","wikidata":"https://www.wikidata.org/wiki/Q2695010","display_name":"Allylic rearrangement","level":3,"score":0.8374999761581421},{"id":"https://openalex.org/C181647583","wikidata":"https://www.wikidata.org/wiki/Q903429","display_name":"Stereoselectivity","level":3,"score":0.8284000158309937},{"id":"https://openalex.org/C486523","wikidata":"https://www.wikidata.org/wiki/Q494483","display_name":"Enantiomer","level":2,"score":0.6347000002861023},{"id":"https://openalex.org/C2780997848","wikidata":"https://www.wikidata.org/wiki/Q407627","display_name":"Azide","level":2,"score":0.6233999729156494},{"id":"https://openalex.org/C2777814067","wikidata":"https://www.wikidata.org/wiki/Q1752317","display_name":"Tandem","level":2,"score":0.6187000274658203},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.5784000158309937},{"id":"https://openalex.org/C58548122","wikidata":"https://www.wikidata.org/wiki/Q838390","display_name":"Cascade reaction","level":3,"score":0.5529999732971191},{"id":"https://openalex.org/C129694887","wikidata":"https://www.wikidata.org/wiki/Q47455153","display_name":"Stereoisomerism","level":3,"score":0.44359999895095825},{"id":"https://openalex.org/C2778112365","wikidata":"https://www.wikidata.org/wiki/Q3511065","display_name":"Sequence (biology)","level":2,"score":0.36500000953674316},{"id":"https://openalex.org/C105768512","wikidata":"https://www.wikidata.org/wiki/Q7458208","display_name":"Reaction intermediate","level":3,"score":0.30959999561309814},{"id":"https://openalex.org/C32909587","wikidata":"https://www.wikidata.org/wiki/Q11369","display_name":"Molecule","level":2,"score":0.295199990272522},{"id":"https://openalex.org/C96350342","wikidata":"https://www.wikidata.org/wiki/Q905087","display_name":"Cope rearrangement","level":2,"score":0.2800999879837036},{"id":"https://openalex.org/C114373084","wikidata":"https://www.wikidata.org/wiki/Q273499","display_name":"Chemical synthesis","level":3,"score":0.2745000123977661},{"id":"https://openalex.org/C2780129066","wikidata":"https://www.wikidata.org/wiki/Q192596","display_name":"Aliphatic compound","level":3,"score":0.2676999866962433},{"id":"https://openalex.org/C65024703","wikidata":"https://www.wikidata.org/wiki/Q373406","display_name":"Reaction mechanism","level":3,"score":0.25619998574256897},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.2535000145435333},{"id":"https://openalex.org/C36674120","wikidata":"https://www.wikidata.org/wiki/Q370228","display_name":"Isotopic labeling","level":2,"score":0.25130000710487366}],"mesh":[],"locations_count":1,"locations":[{"id":"doi:10.1021/acs.orglett.6c04045","doi":"https://doi.org/10.1021/acs.orglett.6c04045","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.orglett.6c04045","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"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":37,"referenced_works":["https://openalex.org/W1959482694","https://openalex.org/W1978167028","https://openalex.org/W2006488658","https://openalex.org/W2007161023","https://openalex.org/W2014385810","https://openalex.org/W2026007745","https://openalex.org/W2027424563","https://openalex.org/W2036885659","https://openalex.org/W2063126484","https://openalex.org/W2065862219","https://openalex.org/W2074102667","https://openalex.org/W2080424665","https://openalex.org/W2082427343","https://openalex.org/W2146318727","https://openalex.org/W2161515135","https://openalex.org/W2214324991","https://openalex.org/W2284217991","https://openalex.org/W2317366066","https://openalex.org/W2323310309","https://openalex.org/W2504411034","https://openalex.org/W2742572572","https://openalex.org/W2785620482","https://openalex.org/W2806340381","https://openalex.org/W2899874192","https://openalex.org/W2913271408","https://openalex.org/W2931324099","https://openalex.org/W2955418869","https://openalex.org/W2969542994","https://openalex.org/W3001075273","https://openalex.org/W3016196282","https://openalex.org/W3017372962","https://openalex.org/W3111545283","https://openalex.org/W3166878392","https://openalex.org/W3169924809","https://openalex.org/W4283837121","https://openalex.org/W4388524730","https://openalex.org/W4406808287"],"related_works":["https://openalex.org/W2931324099","https://openalex.org/W2797496031","https://openalex.org/W2952597721","https://openalex.org/W2089510840","https://openalex.org/W7117516073","https://openalex.org/W2950804734","https://openalex.org/W2082427343","https://openalex.org/W2952203356","https://openalex.org/W2621262021","https://openalex.org/W1967606898"],"abstract_inverted_index":{"Abstract":[0],"A":[1,41],"tandem":[2,54],"Ru-catalyzed":[3,18],"alkene":[4,19],"isomerization/Winstein":[5],"rearrangement":[6],"sequence":[7],"enables":[8],"the":[9,33,37,53],"stereoselective":[10],"synthesis":[11],"of":[12,47,59],"E-allylic":[13],"azides":[14],"from":[15],"alkenyl":[16],"azides.":[17],"isomerization":[20],"generates":[21],"an":[22],"allylic":[23],"azide":[24],"intermediate":[25],"that":[26],"undergoes":[27],"a":[28,65],"spontaneous":[29],"[3,3]-sigmatropic":[30],"rearrangement,":[31],"shifting":[32],"Winstein":[34],"equilibrium":[35],"toward":[36],"thermodynamically":[38],"favored":[39],"product.":[40],"stereochemical":[42],"investigation":[43],"revealed":[44],"partial":[45],"erosion":[46],"enantiomeric":[48],"purity,":[49],"providing":[50],"insight":[51],"into":[52],"process.":[55],"The":[56],"synthetic":[57],"utility":[58],"this":[60],"method":[61],"was":[62],"demonstrated":[63],"through":[64],"scale-up":[66],"experiment":[67],"and":[68],"one-pot":[69],"downstream":[70],"transformations.":[71]},"counts_by_year":[],"updated_date":"2026-11-11T12:16:26.678958","created_date":"2026-11-10T00:00:00"}
