{"id":"https://openalex.org/W1980636601","doi":"https://doi.org/10.1021/ja203171x","title":"A New Strategy for the Synthesis of Chiral \u03b2-Alkynyl Esters via Sequential Palladium and Copper Catalysis","display_name":"A New Strategy for the Synthesis of Chiral \u03b2-Alkynyl Esters via Sequential Palladium and Copper Catalysis","publication_year":2011,"publication_date":"2011-05-11","ids":{"openalex":"https://openalex.org/W1980636601","doi":"https://doi.org/10.1021/ja203171x","mag":"1980636601","pmid":"https://pubmed.ncbi.nlm.nih.gov/21557627","pmcid":"https://www.ncbi.nlm.nih.gov/pmc/articles/3235047"},"language":"en","primary_location":{"id":"doi:10.1021/ja203171x","doi":"https://doi.org/10.1021/ja203171x","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja203171x","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":true,"oa_status":"green","oa_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/3235047","any_repository_has_fulltext":true},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5032412691","display_name":"Barry M. Trost","orcid":"https://orcid.org/0000-0001-7369-9121","observed_orcids":["https://orcid.org/0000-0001-7369-9121"]},"institutions":[{"id":"https://openalex.org/I97018004","display_name":"Stanford University","ror":"https://ror.org/00f54p054","country_code":"US","type":"education","lineage":["https://openalex.org/I97018004"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"Barry M. Trost","raw_affiliation_strings":["Department of Chemistry, Stanford University, Stanford, California 94305-5080, United States","Department of Chemistry, Stanford University, Stanford, California 94305-5080,#R#United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Stanford University, Stanford, California 94305-5080, United States","institution_ids":["https://openalex.org/I97018004"]},{"raw_affiliation_string":"Department of Chemistry, Stanford University, Stanford, California 94305-5080,#R#United States","institution_ids":["https://openalex.org/I97018004"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5032586778","display_name":"Benjamin R. Taft","orcid":"https://orcid.org/0000-0002-1129-7618","observed_orcids":["https://orcid.org/0000-0002-1129-7618"]},"institutions":[{"id":"https://openalex.org/I97018004","display_name":"Stanford University","ror":"https://ror.org/00f54p054","country_code":"US","type":"education","lineage":["https://openalex.org/I97018004"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Benjamin R. Taft","raw_affiliation_strings":["Department of Chemistry, Stanford University, Stanford, California 94305-5080, United States","Department of Chemistry, Stanford University, Stanford, California 94305-5080,#R#United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Stanford University, Stanford, California 94305-5080, United States","institution_ids":["https://openalex.org/I97018004"]},{"raw_affiliation_string":"Department of Chemistry, Stanford University, Stanford, California 94305-5080,#R#United States","institution_ids":["https://openalex.org/I97018004"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5077976349","display_name":"James T. Masters","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I97018004","display_name":"Stanford University","ror":"https://ror.org/00f54p054","country_code":"US","type":"education","lineage":["https://openalex.org/I97018004"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"James T. Masters","raw_affiliation_strings":["Department of Chemistry, Stanford University, Stanford, California 94305-5080, United States","Department of Chemistry, Stanford University, Stanford, California 94305-5080,#R#United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Stanford University, Stanford, California 94305-5080, United States","institution_ids":["https://openalex.org/I97018004"]},{"raw_affiliation_string":"Department of Chemistry, Stanford University, Stanford, California 94305-5080,#R#United States","institution_ids":["https://openalex.org/I97018004"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5058300825","display_name":"Jean\u2010Philip Lumb","orcid":"https://orcid.org/0000-0002-9283-1199","observed_orcids":["https://orcid.org/0000-0002-9283-1199"]},"institutions":[{"id":"https://openalex.org/I97018004","display_name":"Stanford University","ror":"https://ror.org/00f54p054","country_code":"US","type":"education","lineage":["https://openalex.org/I97018004"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Jean-Philip Lumb","raw_affiliation_strings":["Department of Chemistry, Stanford University, Stanford, California 94305-5080, United States","Department of Chemistry, Stanford University, Stanford, California 94305-5080,#R#United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Stanford University, Stanford, California 94305-5080, United States","institution_ids":["https://openalex.org/I97018004"]},{"raw_affiliation_string":"Department of Chemistry, Stanford University, Stanford, California 94305-5080,#R#United States","institution_ids":["https://openalex.org/I97018004"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":["https://openalex.org/A5032412691"],"corresponding_institution_ids":["https://openalex.org/I97018004"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":2.8556,"has_fulltext":false,"cited_by_count":53,"citation_normalized_percentile":{"value":0.89960838,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":88,"max":99},"biblio":{"volume":"133","issue":"22","first_page":"8502","last_page":"8505"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10013","display_name":"Asymmetric Synthesis and Catalysis","score":0.49630001187324524,"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":0.49630001187324524,"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":0.34450000524520874,"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/T10871","display_name":"Catalytic Alkyne Reactions","score":0.13210000097751617,"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/terminal-alkynes","display_name":"terminal alkynes","score":0.8700000047683716},{"id":"https://openalex.org/keywords/asymmetric-synthesis","display_name":"asymmetric synthesis","score":0.8209999799728394},{"id":"https://openalex.org/keywords/allylic-carbonates","display_name":"allylic carbonates","score":0.8960000276565552},{"id":"https://openalex.org/keywords/chiral-heterocycles","display_name":"chiral heterocycles","score":0.8420000076293945}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9472630023956299},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.7270694971084595},{"id":"https://openalex.org/C502130503","wikidata":"https://www.wikidata.org/wiki/Q1089","display_name":"Palladium","level":3,"score":0.6724512577056885},{"id":"https://openalex.org/C120095180","wikidata":"https://www.wikidata.org/wiki/Q2695010","display_name":"Allylic rearrangement","level":3,"score":0.6294361352920532},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.6090458035469055},{"id":"https://openalex.org/C2781076698","wikidata":"https://www.wikidata.org/wiki/Q718074","display_name":"Aryl","level":3,"score":0.5767515301704407},{"id":"https://openalex.org/C118792377","wikidata":"https://www.wikidata.org/wiki/Q108584245","display_name":"Selectivity","level":3,"score":0.5501936674118042},{"id":"https://openalex.org/C2780263894","wikidata":"https://www.wikidata.org/wiki/Q335268","display_name":"Alkyl","level":2,"score":0.500720739364624},{"id":"https://openalex.org/C2779012754","wikidata":"https://www.wikidata.org/wiki/Q159226","display_name":"Alkyne","level":3,"score":0.49495476484298706},{"id":"https://openalex.org/C197336794","wikidata":"https://www.wikidata.org/wiki/Q5161150","display_name":"Conjugate","level":2,"score":0.44891130924224854},{"id":"https://openalex.org/C124668440","wikidata":"https://www.wikidata.org/wiki/Q2305173","display_name":"Chirality (physics)","level":5,"score":0.4290924668312073},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.38436612486839294},{"id":"https://openalex.org/C134306372","wikidata":"https://www.wikidata.org/wiki/Q7754","display_name":"Mathematical analysis","level":1,"score":0.0},{"id":"https://openalex.org/C33923547","wikidata":"https://www.wikidata.org/wiki/Q395","display_name":"Mathematics","level":0,"score":0.0},{"id":"https://openalex.org/C121332964","wikidata":"https://www.wikidata.org/wiki/Q413","display_name":"Physics","level":0,"score":0.0},{"id":"https://openalex.org/C52703039","wikidata":"https://www.wikidata.org/wiki/Q5101837","display_name":"Chiral symmetry breaking","level":3,"score":0.0},{"id":"https://openalex.org/C62520636","wikidata":"https://www.wikidata.org/wiki/Q944","display_name":"Quantum mechanics","level":1,"score":0.0},{"id":"https://openalex.org/C7602139","wikidata":"https://www.wikidata.org/wiki/Q6718","display_name":"Quark","level":2,"score":0.0},{"id":"https://openalex.org/C20621625","wikidata":"https://www.wikidata.org/wiki/Q6961432","display_name":"Nambu\u2013Jona-Lasinio model","level":4,"score":0.0}],"mesh":[{"descriptor_ui":"D000480","descriptor_name":"Alkynes","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":false},{"descriptor_ui":"D000480","descriptor_name":"Alkynes","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":"D003300","descriptor_name":"Copper","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D004952","descriptor_name":"Esters","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D004952","descriptor_name":"Esters","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D010165","descriptor_name":"Palladium","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},{"descriptor_ui":"D015394","descriptor_name":"Molecular Structure","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":4,"locations":[{"id":"doi:10.1021/ja203171x","doi":"https://doi.org/10.1021/ja203171x","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja203171x","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:21557627","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/21557627","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:2376123","doi":null,"is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/3235047","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:3235047","doi":null,"is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/3235047","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:2376123","doi":null,"is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/3235047","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/G2190425771","display_name":"Novel Approaches for Antitumor and Antiviral Agents","funder_award_id":"R01GM033049","funder_id":"https://openalex.org/F4320337354","funder_display_name":"National Institute of General Medical Sciences"},{"id":"https://openalex.org/G38875570","display_name":null,"funder_award_id":"GM 33049","funder_id":"https://openalex.org/F4320337354","funder_display_name":"National Institute of General Medical Sciences"},{"id":"https://openalex.org/G5775877020","display_name":null,"funder_award_id":"GM083428","funder_id":"https://openalex.org/F4320337354","funder_display_name":"National Institute of General Medical Sciences"},{"id":"https://openalex.org/G6379325856","display_name":null,"funder_award_id":"CA137999","funder_id":"https://openalex.org/F4320337351","funder_display_name":"National Cancer Institute"},{"id":"https://openalex.org/G840413212","display_name":"Enantioselective Total Synthesis of Citrinadin A","funder_award_id":"F32CA137999","funder_id":"https://openalex.org/F4320337351","funder_display_name":"National Cancer Institute"},{"id":"https://openalex.org/G8711003561","display_name":"Synthesis of Amphidinolide N","funder_award_id":"F32GM083428","funder_id":"https://openalex.org/F4320337354","funder_display_name":"National Institute of General Medical Sciences"}],"funders":[{"id":"https://openalex.org/F4320306076","display_name":"National Science Foundation","ror":"https://ror.org/021nxhr62"},{"id":"https://openalex.org/F4320332161","display_name":"National Institutes of Health","ror":"https://ror.org/01cwqze88"},{"id":"https://openalex.org/F4320337351","display_name":"National Cancer Institute","ror":"https://ror.org/040gcmg81"},{"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":50,"referenced_works":["https://openalex.org/W630945920","https://openalex.org/W1852920733","https://openalex.org/W1963659623","https://openalex.org/W1966412406","https://openalex.org/W1972806401","https://openalex.org/W1972881351","https://openalex.org/W1989772178","https://openalex.org/W1990585247","https://openalex.org/W1994884961","https://openalex.org/W1996565721","https://openalex.org/W2003747243","https://openalex.org/W2017339707","https://openalex.org/W2024847994","https://openalex.org/W2035598295","https://openalex.org/W2042286819","https://openalex.org/W2048509735","https://openalex.org/W2058743330","https://openalex.org/W2061671671","https://openalex.org/W2062789199","https://openalex.org/W2070763318","https://openalex.org/W2070922428","https://openalex.org/W2071804528","https://openalex.org/W2081966254","https://openalex.org/W2085435229","https://openalex.org/W2085836399","https://openalex.org/W2086355314","https://openalex.org/W2088623222","https://openalex.org/W2105787857","https://openalex.org/W2107323023","https://openalex.org/W2121056473","https://openalex.org/W2161491245","https://openalex.org/W2161543055","https://openalex.org/W2162449746","https://openalex.org/W2166730934","https://openalex.org/W2168701747","https://openalex.org/W2332413183","https://openalex.org/W2432348959","https://openalex.org/W2949095987","https://openalex.org/W2949369586","https://openalex.org/W2949774588","https://openalex.org/W2950139531","https://openalex.org/W2950578611","https://openalex.org/W2951234141","https://openalex.org/W2951818525","https://openalex.org/W2951900169","https://openalex.org/W2952143579","https://openalex.org/W2952231802","https://openalex.org/W2952277467","https://openalex.org/W2953368889","https://openalex.org/W4229731655"],"related_works":["https://openalex.org/W2950711253","https://openalex.org/W2415455624","https://openalex.org/W4313533024","https://openalex.org/W2168872924","https://openalex.org/W2501417664","https://openalex.org/W2897024212","https://openalex.org/W2949875555","https://openalex.org/W2080115564","https://openalex.org/W4403058740","https://openalex.org/W2232751126"],"abstract_inverted_index":{"A":[0],"new":[1],"strategy":[2],"for":[3,79,114],"the":[4,80,98,118],"synthesis":[5],"of":[6,38,51,95,104,117,124],"chiral":[7,40],"\u03b2-alkynyl":[8,90,119],"esters":[9,91,120],"which":[10,60],"relies":[11],"on":[12],"sequential":[13],"Pd":[14],"and":[15,25,109,111],"Cu":[16],"catalysis":[17],"is":[18],"reported.":[19],"Terminal":[20],"alkynes":[21,55],"bearing":[22],"aryl,":[23],"alkyl,":[24],"silyl":[26],"groups":[27],"can":[28],"be":[29],"employed":[30],"without":[31],"prior":[32],"activation":[33],"yielding":[34,89],"a":[35,47,101,122],"wide":[36,102],"range":[37,103],"important":[39],"building":[41],"blocks.":[42],"The":[43],"reaction":[44],"sequence":[45],"utilizes":[46],"robust":[48],"Pd(II)-catalyzed":[49],"hydroalkynylation":[50],"ynoates":[52],"with":[53,76,86,92],"terminal":[54],"providing":[56],"geometrically":[57],"pure":[58],"ynenoates":[59,74],"are":[61],"readily":[62],"reduced":[63],"by":[64],"CuH.":[65],"In":[66],"contrast":[67],"to":[68,73],"previous":[69],"reports,":[70],"where":[71],"additions":[72],"proceed":[75],"marginal":[77],"preference":[78],"1,6-pathway,":[81],"this":[82],"conjugate":[83],"reduction":[84],"occurs":[85],"high":[87],"1,4-selectivity":[88],"excellent":[93],"levels":[94],"enantioselectivity.":[96],"Importantly,":[97],"method":[99],"tolerates":[100],"functionality,":[105],"including":[106],"allylic":[107],"carbonates":[108],"carbamates,":[110],"thus":[112],"allows":[113],"rapid":[115],"elaboration":[116],"into":[121],"variety":[123],"chiral,":[125],"substituted":[126],"heterocycles.":[127]},"counts_by_year":[{"year":2025,"cited_by_count":1},{"year":2023,"cited_by_count":5},{"year":2022,"cited_by_count":4},{"year":2021,"cited_by_count":3},{"year":2020,"cited_by_count":1},{"year":2019,"cited_by_count":2},{"year":2018,"cited_by_count":5},{"year":2017,"cited_by_count":4},{"year":2016,"cited_by_count":4},{"year":2015,"cited_by_count":5},{"year":2014,"cited_by_count":9},{"year":2013,"cited_by_count":7},{"year":2012,"cited_by_count":2}],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2016-06-24T00:00:00"}