{"id":"https://openalex.org/W2020848534","doi":"https://doi.org/10.1021/ol025825n","title":"BINOL-Catalyzed Highly Enantioselective Terminal Alkyne Additions to Aromatic Aldehydes","display_name":"BINOL-Catalyzed Highly Enantioselective Terminal Alkyne Additions to Aromatic Aldehydes","publication_year":2002,"publication_date":"2002-05-01","ids":{"openalex":"https://openalex.org/W2020848534","doi":"https://doi.org/10.1021/ol025825n","mag":"2020848534","pmid":"https://pubmed.ncbi.nlm.nih.gov/12027631"},"language":"en","primary_location":{"id":"doi:10.1021/ol025825n","doi":"https://doi.org/10.1021/ol025825n","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ol025825n","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","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":null,"display_name":"David Moore","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I51556381","display_name":"University of Virginia","ror":"https://ror.org/0153tk833","country_code":"US","type":"education","lineage":["https://openalex.org/I51556381"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"David Moore","raw_affiliation_strings":["Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904-4319","Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904-4319, USA"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904-4319","institution_ids":["https://openalex.org/I51556381"]},{"raw_affiliation_string":"Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904-4319, USA","institution_ids":["https://openalex.org/I51556381"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5031341127","display_name":"Lin Pu","orcid":"https://orcid.org/0000-0001-8698-3228","observed_orcids":["https://orcid.org/0000-0001-8698-3228"]},"institutions":[{"id":"https://openalex.org/I51556381","display_name":"University of Virginia","ror":"https://ror.org/0153tk833","country_code":"US","type":"education","lineage":["https://openalex.org/I51556381"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Lin Pu","raw_affiliation_strings":["Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904-4319"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904-4319","institution_ids":["https://openalex.org/I51556381"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":[],"corresponding_institution_ids":["https://openalex.org/I51556381"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":9.5658,"has_fulltext":false,"cited_by_count":171,"citation_normalized_percentile":{"value":0.99102295,"is_in_top_1_percent":true,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":88,"max":99},"biblio":{"volume":"4","issue":"11","first_page":"1855","last_page":"1857"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10013","display_name":"Asymmetric Synthesis and Catalysis","score":0.9980000257492065,"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":0.9980000257492065,"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/T11281","display_name":"Asymmetric Hydrogenation and Catalysis","score":0.0010000000474974513,"subfield":{"id":"https://openalex.org/subfields/1604","display_name":"Inorganic 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/T13115","display_name":"Axial and Atropisomeric Chirality Synthesis","score":0.0003000000142492354,"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/binol-ligands","display_name":"BINOL ligands","score":0.9240000247955322},{"id":"https://openalex.org/keywords/titanium-isopropoxide","display_name":"titanium isopropoxide","score":0.7440000176429749},{"id":"https://openalex.org/keywords/asymmetric-catalysis","display_name":"asymmetric catalysis","score":0.8579999804496765},{"id":"https://openalex.org/keywords/terminal-alkynes","display_name":"terminal alkynes","score":0.8450000286102295},{"id":"https://openalex.org/keywords/aromatic-aldehydes","display_name":"aromatic aldehydes","score":0.9829999804496765},{"id":"https://openalex.org/keywords/enantioselective-addition","display_name":"enantioselective addition","score":0.8330000042915344},{"id":"https://openalex.org/keywords/chiral-auxiliaries","display_name":"chiral auxiliaries","score":0.4880000054836273}],"concepts":[{"id":"https://openalex.org/C146686406","wikidata":"https://www.wikidata.org/wiki/Q898628","display_name":"Enantioselective synthesis","level":3,"score":0.9283093214035034},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9006029367446899},{"id":"https://openalex.org/C2779012754","wikidata":"https://www.wikidata.org/wiki/Q159226","display_name":"Alkyne","level":3,"score":0.8653409481048584},{"id":"https://openalex.org/C2779627003","wikidata":"https://www.wikidata.org/wiki/Q415602","display_name":"Acetylide","level":2,"score":0.8329642415046692},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.8087983131408691},{"id":"https://openalex.org/C40875361","wikidata":"https://www.wikidata.org/wiki/Q2356542","display_name":"Reagent","level":2,"score":0.6998723745346069},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.551160454750061},{"id":"https://openalex.org/C116569031","wikidata":"https://www.wikidata.org/wiki/Q899107","display_name":"Ligand (biochemistry)","level":3,"score":0.49184131622314453},{"id":"https://openalex.org/C535196362","wikidata":"https://www.wikidata.org/wiki/Q758","display_name":"Zinc","level":2,"score":0.47647783160209656},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.4373191297054291},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.28024306893348694},{"id":"https://openalex.org/C170493617","wikidata":"https://www.wikidata.org/wiki/Q208467","display_name":"Receptor","level":2,"score":0.0},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.0}],"mesh":[{"descriptor_ui":"D001384","descriptor_name":"Azetidines","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":"D005612","descriptor_name":"Freeze Drying","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D006900","descriptor_name":"Hydroxylation","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D010880","descriptor_name":"Piperidines","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D013237","descriptor_name":"Stereoisomerism","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D020578","descriptor_name":"Sphingomonas","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":true}],"locations_count":2,"locations":[{"id":"doi:10.1021/ol025825n","doi":"https://doi.org/10.1021/ol025825n","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ol025825n","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"},{"id":"pmid:12027631","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/12027631","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":"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":11,"referenced_works":["https://openalex.org/W1965453006","https://openalex.org/W1999408378","https://openalex.org/W2004562493","https://openalex.org/W2021233443","https://openalex.org/W2027994859","https://openalex.org/W2088390324","https://openalex.org/W2158303674","https://openalex.org/W2160489485","https://openalex.org/W2950600127","https://openalex.org/W2952391291","https://openalex.org/W4256559718"],"related_works":["https://openalex.org/W2153344602","https://openalex.org/W2951684163","https://openalex.org/W2045353829","https://openalex.org/W2952259646","https://openalex.org/W1999154507","https://openalex.org/W1977150223","https://openalex.org/W2949422677","https://openalex.org/W2949507873","https://openalex.org/W2950788300","https://openalex.org/W2028991111"],"abstract_inverted_index":{"[reaction:":[0],"see":[1],"text]":[2],"The":[3],"readily":[4],"available":[5],"BINOL":[6],"ligand":[7],"in":[8],"combination":[9],"with":[10,25,55],"Ti(O(i)Pr)(4)":[11],"was":[12],"found":[13],"to":[14,49],"catalyze":[15],"the":[16,38,41,45,65],"highly":[17],"enantioselective":[18],"reaction":[19],"(92-98%":[20],"ee)":[21],"of":[22,32,40,68],"terminal":[23],"alkynes":[24],"aromatic":[26],"aldehydes":[27,50],"that":[28],"contain":[29],"a":[30],"variety":[31],"substituents":[33],"and":[34],"substitution":[35],"patterns.":[36],"After":[37],"preparation":[39],"zinc":[42],"acetylide":[43],"reagent,":[44],"catalytic":[46],"asymmetric":[47,66],"addition":[48],"proceeded":[51],"at":[52],"room":[53],"temperature":[54],"excellent":[56],"stereocontrol.":[57],"This":[58],"simple":[59],"catalyst":[60],"system":[61],"is":[62],"practical":[63],"for":[64],"synthesis":[67],"chiral":[69],"propargylic":[70],"alcohols.":[71]},"counts_by_year":[{"year":2024,"cited_by_count":2},{"year":2023,"cited_by_count":1},{"year":2022,"cited_by_count":2},{"year":2021,"cited_by_count":1},{"year":2020,"cited_by_count":1},{"year":2019,"cited_by_count":1},{"year":2018,"cited_by_count":1},{"year":2017,"cited_by_count":1},{"year":2016,"cited_by_count":8},{"year":2015,"cited_by_count":11},{"year":2014,"cited_by_count":8},{"year":2013,"cited_by_count":6},{"year":2012,"cited_by_count":6}],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2016-06-24T00:00:00"}