{"id":"https://openalex.org/W1976431028","doi":"https://doi.org/10.1021/ja058077g","title":"Catalytic, Enantioselective [4 + 2]-Cycloadditions of Ketene Enolates and o-Quinones: Efficient Entry to Chiral, \u03b1-Oxygenated Carboxylic Acid Derivatives","display_name":"Catalytic, Enantioselective [4 + 2]-Cycloadditions of Ketene Enolates and o-Quinones: Efficient Entry to Chiral, \u03b1-Oxygenated Carboxylic Acid Derivatives","publication_year":2006,"publication_date":"2006-01-21","ids":{"openalex":"https://openalex.org/W1976431028","doi":"https://doi.org/10.1021/ja058077g","mag":"1976431028","pmid":"https://pubmed.ncbi.nlm.nih.gov/16464078"},"language":"en","primary_location":{"id":"doi:10.1021/ja058077g","doi":"https://doi.org/10.1021/ja058077g","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja058077g","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","indexed_in":["crossref","pubmed"],"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/A5017509159","display_name":"Tefsit Bekele","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I145311948","display_name":"Johns Hopkins University","ror":"https://ror.org/00za53h95","country_code":"US","type":"education","lineage":["https://openalex.org/I145311948"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Tefsit Bekele","raw_affiliation_strings":["Department of Chemistry, New Chemistry Building, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland, 21218"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, New Chemistry Building, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland, 21218","institution_ids":["https://openalex.org/I145311948"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5010893381","display_name":"Meha H. Shah","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I145311948","display_name":"Johns Hopkins University","ror":"https://ror.org/00za53h95","country_code":"US","type":"education","lineage":["https://openalex.org/I145311948"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Meha H. Shah","raw_affiliation_strings":["Department of Chemistry, New Chemistry Building, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland, 21218"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, New Chemistry Building, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland, 21218","institution_ids":["https://openalex.org/I145311948"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5078022317","display_name":"Jamison D. Wolfer","orcid":"https://orcid.org/0000-0003-2843-0179","observed_orcids":["https://orcid.org/0000-0003-2843-0179"]},"institutions":[{"id":"https://openalex.org/I145311948","display_name":"Johns Hopkins University","ror":"https://ror.org/00za53h95","country_code":"US","type":"education","lineage":["https://openalex.org/I145311948"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Jamison Wolfer","raw_affiliation_strings":["Department of Chemistry, New Chemistry Building, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland, 21218"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, New Chemistry Building, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland, 21218","institution_ids":["https://openalex.org/I145311948"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5066119178","display_name":"Ciby J. Abraham","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I145311948","display_name":"Johns Hopkins University","ror":"https://ror.org/00za53h95","country_code":"US","type":"education","lineage":["https://openalex.org/I145311948"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Ciby J. Abraham","raw_affiliation_strings":["Department of Chemistry, New Chemistry Building, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland, 21218"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, New Chemistry Building, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland, 21218","institution_ids":["https://openalex.org/I145311948"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5071510993","display_name":"Anthony Weatherwax","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I145311948","display_name":"Johns Hopkins University","ror":"https://ror.org/00za53h95","country_code":"US","type":"education","lineage":["https://openalex.org/I145311948"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Anthony Weatherwax","raw_affiliation_strings":["Department of Chemistry, New Chemistry Building, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland, 21218"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, New Chemistry Building, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland, 21218","institution_ids":["https://openalex.org/I145311948"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5046784729","display_name":"Thomas Lectka","orcid":"https://orcid.org/0000-0003-3088-6714","observed_orcids":["https://orcid.org/0000-0003-3088-6714"]},"institutions":[{"id":"https://openalex.org/I145311948","display_name":"Johns Hopkins University","ror":"https://ror.org/00za53h95","country_code":"US","type":"education","lineage":["https://openalex.org/I145311948"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Thomas Lectka","raw_affiliation_strings":["Department of Chemistry, New Chemistry Building, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland, 21218"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, New Chemistry Building, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland, 21218","institution_ids":["https://openalex.org/I145311948"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":[],"corresponding_institution_ids":["https://openalex.org/I145311948"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":4.4919,"has_fulltext":false,"cited_by_count":115,"citation_normalized_percentile":{"value":0.95248043,"is_in_top_1_percent":false,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":94,"max":99},"biblio":{"volume":"128","issue":"6","first_page":"1810","last_page":"1811"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10013","display_name":"Asymmetric Synthesis and Catalysis","score":0.9961000084877014,"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":0.9961000084877014,"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/T13859","display_name":"Organic Chemistry Synthesis Methods","score":0.0017999999690800905,"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":0.0008999999845400453,"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/diels-alder-reaction","display_name":"Diels-Alder reaction","score":0.9070000052452087},{"id":"https://openalex.org/keywords/o-quinones","display_name":"o-quinones","score":0.996999979019165},{"id":"https://openalex.org/keywords/asymmetric-catalysis","display_name":"asymmetric catalysis","score":0.9049999713897705},{"id":"https://openalex.org/keywords/cinchona-alkaloid-catalysts","display_name":"cinchona alkaloid catalysts","score":0.9089999794960022},{"id":"https://openalex.org/keywords/asymmetric-synthesis","display_name":"asymmetric synthesis","score":0.578000009059906}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9655274152755737},{"id":"https://openalex.org/C2778874822","wikidata":"https://www.wikidata.org/wiki/Q368158","display_name":"Ketene","level":2,"score":0.9402059316635132},{"id":"https://openalex.org/C146686406","wikidata":"https://www.wikidata.org/wiki/Q898628","display_name":"Enantioselective synthesis","level":3,"score":0.9100724458694458},{"id":"https://openalex.org/C2777797831","wikidata":"https://www.wikidata.org/wiki/Q160090","display_name":"Cinchona","level":4,"score":0.7507999539375305},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.640666127204895},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.6173431873321533},{"id":"https://openalex.org/C486523","wikidata":"https://www.wikidata.org/wiki/Q494483","display_name":"Enantiomer","level":2,"score":0.6068784594535828},{"id":"https://openalex.org/C2779074116","wikidata":"https://www.wikidata.org/wiki/Q134856","display_name":"Carboxylic acid","level":2,"score":0.5645231008529663},{"id":"https://openalex.org/C3141732","wikidata":"https://www.wikidata.org/wiki/Q568761","display_name":"Enantiomeric excess","level":4,"score":0.4849686622619629},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.3624070882797241}],"mesh":[{"descriptor_ui":"D002264","descriptor_name":"Carboxylic Acids","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D002384","descriptor_name":"Catalysis","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D002703","descriptor_name":"Chloranil","qualifier_ui":"Q000031","qualifier_name":"analogs & derivatives","is_major_topic":false},{"descriptor_ui":"D002703","descriptor_name":"Chloranil","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D003500","descriptor_name":"Cyclization","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D005030","descriptor_name":"Ethylenes","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D007659","descriptor_name":"Ketones","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D010084","descriptor_name":"Oxidation-Reduction","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D011809","descriptor_name":"Quinones","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D013237","descriptor_name":"Stereoisomerism","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":2,"locations":[{"id":"doi:10.1021/ja058077g","doi":"https://doi.org/10.1021/ja058077g","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja058077g","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:16464078","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/16464078","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"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G5299774889","display_name":null,"funder_award_id":"GM064559","funder_id":"https://openalex.org/F4320337354","funder_display_name":"National Institute of General Medical Sciences"},{"id":"https://openalex.org/G5674964563","display_name":"Heterocumulenes in Asymmetric Catalysis","funder_award_id":"R01GM064559","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":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":2,"referenced_works":["https://openalex.org/W2085335257","https://openalex.org/W2951345878"],"related_works":["https://openalex.org/W7096114612","https://openalex.org/W2626424521","https://openalex.org/W2055190705","https://openalex.org/W1995740330","https://openalex.org/W1963575269","https://openalex.org/W2150260304","https://openalex.org/W2952647520","https://openalex.org/W4412892118","https://openalex.org/W2951794757","https://openalex.org/W2950245865"],"abstract_inverted_index":{"We":[0],"report":[1],"catalytic,":[2],"enantioselective":[3],"[4":[4],"+":[5],"2]-cycloadditions":[6],"of":[7,51,67,77],"o-quinones":[8],"with":[9],"ketene":[10],"enolates":[11],"(derived":[12],"from":[13],"readily":[14],"available":[15],"acid":[16,80],"chlorides)":[17],"using":[18],"cinchona":[19],"alkaloid":[20],"derivatives":[21],"as":[22],"catalysts":[23],"to":[24,34,48,53,72],"produce":[25],"products":[26],"in":[27,46,64],"high":[28],"enantiomeric":[29],"excess":[30],"(ee)":[31],"and":[32],"good":[33],"excellent":[35],"yields.":[36],"The":[37,56],"thermodynamic":[38],"driving":[39],"force":[40],"for":[41,70],"these":[42],"reactions":[43],"is":[44],"due":[45],"part":[47],"the":[49,54],"restoration":[50],"aromaticity":[52],"products.":[55],"resulting":[57],"chiral,":[58],"bicycloadducts":[59],"can":[60],"be":[61],"synthetically":[62],"manipulated":[63],"a":[65,74],"variety":[66],"useful":[68],"ways,":[69],"example":[71],"provide":[73],"flexible":[75],"synthesis":[76],"alpha-oxygenated":[78],"carboxylic":[79],"derivatives.":[81]},"counts_by_year":[{"year":2026,"cited_by_count":2},{"year":2025,"cited_by_count":2},{"year":2024,"cited_by_count":5},{"year":2023,"cited_by_count":4},{"year":2022,"cited_by_count":5},{"year":2021,"cited_by_count":3},{"year":2020,"cited_by_count":5},{"year":2019,"cited_by_count":6},{"year":2018,"cited_by_count":5},{"year":2017,"cited_by_count":6},{"year":2016,"cited_by_count":6},{"year":2015,"cited_by_count":7},{"year":2014,"cited_by_count":4},{"year":2013,"cited_by_count":6},{"year":2012,"cited_by_count":7}],"updated_date":"2026-11-04T10:54:05.112534","created_date":"2016-06-24T00:00:00"}