{"id":"https://openalex.org/W2015146930","doi":"https://doi.org/10.1021/ja972225o","title":"A Mechanistic and Structural Investigation of the (\u2212)-Sparteine Mediated Asymmetric Benzylic Lithiation Substitution Reactions of N-Boc-N-(p-methoxyphenyl)benzylamine","display_name":"A Mechanistic and Structural Investigation of the (\u2212)-Sparteine Mediated Asymmetric Benzylic Lithiation Substitution Reactions of N-Boc-N-(p-methoxyphenyl)benzylamine","publication_year":1997,"publication_date":"1997-12-01","ids":{"openalex":"https://openalex.org/W2015146930","doi":"https://doi.org/10.1021/ja972225o","mag":"2015146930"},"language":"en","primary_location":{"id":"doi:10.1021/ja972225o","doi":"https://doi.org/10.1021/ja972225o","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja972225o","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"],"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/A5039832158","display_name":"Neil C. Faibish","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I157725225","display_name":"University of Illinois Urbana-Champaign","ror":"https://ror.org/047426m28","country_code":"US","type":"education","lineage":["https://openalex.org/I157725225"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Neil C. Faibish","raw_affiliation_strings":["Contribution from the Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801","institution_ids":["https://openalex.org/I157725225"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5046637540","display_name":"Yong Sun Park","orcid":"https://orcid.org/0000-0002-3111-2385","observed_orcids":["https://orcid.org/0000-0002-3111-2385"]},"institutions":[{"id":"https://openalex.org/I157725225","display_name":"University of Illinois Urbana-Champaign","ror":"https://ror.org/047426m28","country_code":"US","type":"education","lineage":["https://openalex.org/I157725225"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Yong Sun Park","raw_affiliation_strings":["Contribution from the Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801","institution_ids":["https://openalex.org/I157725225"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5103497733","display_name":"Steven Lee","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I157725225","display_name":"University of Illinois Urbana-Champaign","ror":"https://ror.org/047426m28","country_code":"US","type":"education","lineage":["https://openalex.org/I157725225"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Steven Lee","raw_affiliation_strings":["Contribution from the Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801","institution_ids":["https://openalex.org/I157725225"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5072926516","display_name":"Peter Andrew Beak","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I157725225","display_name":"University of Illinois Urbana-Champaign","ror":"https://ror.org/047426m28","country_code":"US","type":"education","lineage":["https://openalex.org/I157725225"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Peter Beak","raw_affiliation_strings":["Contribution from the Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801","institution_ids":["https://openalex.org/I157725225"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":[],"corresponding_institution_ids":["https://openalex.org/I157725225"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":4.4517,"has_fulltext":false,"cited_by_count":104,"citation_normalized_percentile":{"value":0.9544065,"is_in_top_1_percent":false,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":88,"max":99},"biblio":{"volume":"119","issue":"48","first_page":"11561","last_page":"11570"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T12228","display_name":"Coordination Chemistry and Organometallics","score":0.9901999831199646,"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/T12228","display_name":"Coordination Chemistry and Organometallics","score":0.9901999831199646,"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":0.003100000089034438,"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/T12191","display_name":"Chemical Reaction Mechanisms","score":0.0024999999441206455,"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/sparteine","display_name":"sparteine","score":0.8320000171661377},{"id":"https://openalex.org/keywords/n-butyllithium","display_name":"n-butyllithium","score":0.7350000143051147},{"id":"https://openalex.org/keywords/enantioselective-deprotonation","display_name":"enantioselective deprotonation","score":0.9490000009536743},{"id":"https://openalex.org/keywords/lithium-complexation","display_name":"lithium complexation","score":0.4129999876022339},{"id":"https://openalex.org/keywords/absolute-configuration","display_name":"absolute configuration","score":0.5860000252723694},{"id":"https://openalex.org/keywords/tmeda","display_name":"TMEDA","score":0.4569999873638153}],"concepts":[{"id":"https://openalex.org/C2778694420","wikidata":"https://www.wikidata.org/wiki/Q419552","display_name":"Sparteine","level":2,"score":0.9675040245056152},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9648118019104004},{"id":"https://openalex.org/C2776276205","wikidata":"https://www.wikidata.org/wiki/Q424000","display_name":"Benzylamine","level":2,"score":0.9173656105995178},{"id":"https://openalex.org/C118629725","wikidata":"https://www.wikidata.org/wiki/Q2686738","display_name":"Deprotonation","level":3,"score":0.7426357269287109},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.6648755073547363},{"id":"https://openalex.org/C2778541603","wikidata":"https://www.wikidata.org/wiki/Q152763","display_name":"Lithium (medication)","level":2,"score":0.5782341957092285},{"id":"https://openalex.org/C146686406","wikidata":"https://www.wikidata.org/wiki/Q898628","display_name":"Enantioselective synthesis","level":3,"score":0.5160674452781677},{"id":"https://openalex.org/C50027330","wikidata":"https://www.wikidata.org/wiki/Q908086","display_name":"Electrophile","level":3,"score":0.4680855870246887},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.467096745967865},{"id":"https://openalex.org/C66974803","wikidata":"https://www.wikidata.org/wiki/Q10359898","display_name":"Nuclear magnetic resonance spectroscopy","level":2,"score":0.4620359241962433},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.1444825530052185},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.08155789971351624},{"id":"https://openalex.org/C71924100","wikidata":"https://www.wikidata.org/wiki/Q11190","display_name":"Medicine","level":0,"score":0.0},{"id":"https://openalex.org/C134018914","wikidata":"https://www.wikidata.org/wiki/Q162606","display_name":"Endocrinology","level":1,"score":0.0},{"id":"https://openalex.org/C145148216","wikidata":"https://www.wikidata.org/wiki/Q36496","display_name":"Ion","level":2,"score":0.0}],"mesh":[],"locations_count":1,"locations":[{"id":"doi:10.1021/ja972225o","doi":"https://doi.org/10.1021/ja972225o","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja972225o","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"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":50,"referenced_works":["https://openalex.org/W609455602","https://openalex.org/W1971462175","https://openalex.org/W1978140427","https://openalex.org/W1982699960","https://openalex.org/W1984927609","https://openalex.org/W1988050452","https://openalex.org/W1993321508","https://openalex.org/W1996973796","https://openalex.org/W1998000025","https://openalex.org/W2001435415","https://openalex.org/W2004294229","https://openalex.org/W2022654278","https://openalex.org/W2023874741","https://openalex.org/W2030314990","https://openalex.org/W2031070409","https://openalex.org/W2037374748","https://openalex.org/W2038483700","https://openalex.org/W2044428187","https://openalex.org/W2045248298","https://openalex.org/W2050673609","https://openalex.org/W2061727172","https://openalex.org/W2064428889","https://openalex.org/W2076140058","https://openalex.org/W2078945255","https://openalex.org/W2080147054","https://openalex.org/W2082609268","https://openalex.org/W2083646040","https://openalex.org/W2085055231","https://openalex.org/W2093416018","https://openalex.org/W2114955487","https://openalex.org/W2131413357","https://openalex.org/W2146706557","https://openalex.org/W2151613745","https://openalex.org/W2314025403","https://openalex.org/W2314694479","https://openalex.org/W2322188529","https://openalex.org/W2325110236","https://openalex.org/W2949248221","https://openalex.org/W2949402375","https://openalex.org/W2949489215","https://openalex.org/W2949578918","https://openalex.org/W2950548390","https://openalex.org/W2950620014","https://openalex.org/W2950896545","https://openalex.org/W2951540783","https://openalex.org/W2952012113","https://openalex.org/W2952170567","https://openalex.org/W2952299863","https://openalex.org/W3005425261","https://openalex.org/W3021840312"],"related_works":["https://openalex.org/W2949402375","https://openalex.org/W2024444656","https://openalex.org/W2267976313","https://openalex.org/W2086290595","https://openalex.org/W2953351054","https://openalex.org/W2031070409","https://openalex.org/W2038713317","https://openalex.org/W2156064999","https://openalex.org/W2583065060","https://openalex.org/W1971462175"],"abstract_inverted_index":{"Mechanistic":[0],"and":[1,62,84,95,109,124,142],"structural":[2],"studies":[3],"show":[4],"the":[5,9,75,78,81,88,153,158],"high":[6,132],"enantioenrichments":[7],"in":[8,91],"products":[10],"from":[11,30],"lithiation\u2212substitutions":[12],"of":[13,34,80,87,152,157,160],"N":[14,16,99,101],"-Boc-":[15,100],"-(":[17,102],"p":[18,103],"-methoxyphenyl)benzylamine":[19],"(":[20,26,40,56,63,92,96,110,119,125,138,143],"1":[21,35,146,149],")":[22,28,114],"by":[23],"n":[24,116],"-BuLi/(\u2212)-sparteine":[25],"6":[27,45,53,61,68],"arise":[29],"an":[31],"enantioselective":[32],"deprotonation":[33],"to":[36,74,137],"provide":[37,118],"configurationally":[38,162],"stable":[39,163],"R":[41,57,93,106,120,139,144],")-":[42,58,65,94,98,107,112,121,127,140,145],"2":[43,59,66,141],"/":[44,60,67],".":[46],"NMR":[47],"spectroscopy":[48],"establishes":[49],"that":[50],"13":[51],"C,":[52],"Li":[54],"labeled":[55],"S":[64,97,111,126],"are":[69],"monomeric":[70],"with":[71,115,131],"lithium":[72],"complexed":[73],"benzylic":[76],"position,":[77],"carbonyl":[79],"Boc":[82],"group":[83],"(\u2212)-sparteine.":[85],"Deprotonations":[86],"tertiary":[89],"protons":[90],"-methoxyphenyl)-\u03b1-methylbenzylamine":[104],"((":[105],"8":[108,113],"-BuLi/TMEDA":[117],"9":[122,128],"/TMEDA":[123],"/TMEDA,":[129],"respectively,":[130],"enantioenrichments.":[133],"Absolute":[134],"configurations":[135],"assigned":[136],"-":[147],"d":[148],"allow":[150],"analysis":[151],"electrophile":[154],"dependent":[155],"stereochemistry":[156],"reactions":[159],"these":[161],"organolithium":[164],"intermediates.":[165]},"counts_by_year":[{"year":2026,"cited_by_count":1},{"year":2025,"cited_by_count":4},{"year":2023,"cited_by_count":3},{"year":2021,"cited_by_count":1},{"year":2020,"cited_by_count":1},{"year":2019,"cited_by_count":1},{"year":2018,"cited_by_count":4},{"year":2017,"cited_by_count":1},{"year":2015,"cited_by_count":3},{"year":2014,"cited_by_count":8},{"year":2013,"cited_by_count":4},{"year":2012,"cited_by_count":4}],"updated_date":"2026-11-04T10:54:05.112534","created_date":"2016-06-24T00:00:00"}