{"id":"https://openalex.org/W2024444656","doi":"https://doi.org/10.1021/ja9910560","title":"Temperature- and Electrophile-Dependent Stereocontrol: A Structural and Mechanistic Investigation of (\u2212)-Sparteine-Mediated Asymmetric Lithiation\u2212Substitution Sequences of N-Boc-N-(p-Methoxyphenyl)cinnamylamine","display_name":"Temperature- and Electrophile-Dependent Stereocontrol: A Structural and Mechanistic Investigation of (\u2212)-Sparteine-Mediated Asymmetric Lithiation\u2212Substitution Sequences of N-Boc-N-(p-Methoxyphenyl)cinnamylamine","publication_year":1999,"publication_date":"1999-09-29","ids":{"openalex":"https://openalex.org/W2024444656","doi":"https://doi.org/10.1021/ja9910560","mag":"2024444656"},"language":"en","primary_location":{"id":"doi:10.1021/ja9910560","doi":"https://doi.org/10.1021/ja9910560","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja9910560","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/A5087015380","display_name":"Gerald A. Weisenburger","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":"Gerald A. Weisenburger","raw_affiliation_strings":["Contribution from the Department of Chemistry, University of Illinois at UrbanaChampaign, Urbana, Illinois 61801"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Department of Chemistry, University of Illinois at UrbanaChampaign, Urbana, Illinois 61801","institution_ids":["https://openalex.org/I157725225"]}]},{"author_position":"middle","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 UrbanaChampaign, Urbana, Illinois 61801"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Department of Chemistry, University of Illinois at UrbanaChampaign, Urbana, Illinois 61801","institution_ids":["https://openalex.org/I157725225"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5049655181","display_name":"Daniel J. Pippel","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":"Daniel J. Pippel","raw_affiliation_strings":["Contribution from the Department of Chemistry, University of Illinois at UrbanaChampaign, Urbana, Illinois 61801"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Department of Chemistry, University of Illinois at UrbanaChampaign, 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 UrbanaChampaign, Urbana, Illinois 61801"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Department of Chemistry, University of Illinois at UrbanaChampaign, 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":5.5255,"has_fulltext":false,"cited_by_count":65,"citation_normalized_percentile":{"value":0.96923225,"is_in_top_1_percent":false,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":89,"max":97},"biblio":{"volume":"121","issue":"41","first_page":"9522","last_page":"9530"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T12228","display_name":"Coordination Chemistry and Organometallics","score":0.9541000127792358,"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":0.9541000127792358,"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":0.02329999953508377,"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":0.010499999858438969,"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":0.9369999766349792},{"id":"https://openalex.org/keywords/solution-structure","display_name":"solution structure","score":0.6209999918937683},{"id":"https://openalex.org/keywords/dynamic-kinetic-resolution","display_name":"dynamic kinetic resolution","score":0.7080000042915344},{"id":"https://openalex.org/keywords/asymmetric-deprotonation","display_name":"asymmetric deprotonation","score":0.9660000205039978},{"id":"https://openalex.org/keywords/epimerization","display_name":"epimerization","score":0.699999988079071},{"id":"https://openalex.org/keywords/asymmetric-synthesis","display_name":"asymmetric synthesis","score":0.6769999861717224}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9747375845909119},{"id":"https://openalex.org/C2778694420","wikidata":"https://www.wikidata.org/wiki/Q419552","display_name":"Sparteine","level":2,"score":0.930687427520752},{"id":"https://openalex.org/C134195300","wikidata":"https://www.wikidata.org/wiki/Q902071","display_name":"Stereocenter","level":4,"score":0.8327237963676453},{"id":"https://openalex.org/C118629725","wikidata":"https://www.wikidata.org/wiki/Q2686738","display_name":"Deprotonation","level":3,"score":0.6876307725906372},{"id":"https://openalex.org/C146686406","wikidata":"https://www.wikidata.org/wiki/Q898628","display_name":"Enantioselective synthesis","level":3,"score":0.6830427646636963},{"id":"https://openalex.org/C28173026","wikidata":"https://www.wikidata.org/wiki/Q337361","display_name":"Kinetic resolution","level":4,"score":0.6701469421386719},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.658211350440979},{"id":"https://openalex.org/C203130289","wikidata":"https://www.wikidata.org/wiki/Q926272","display_name":"Epimer","level":2,"score":0.6263384819030762},{"id":"https://openalex.org/C50027330","wikidata":"https://www.wikidata.org/wiki/Q908086","display_name":"Electrophile","level":3,"score":0.6083975434303284},{"id":"https://openalex.org/C164361826","wikidata":"https://www.wikidata.org/wiki/Q177604","display_name":"Alkylation","level":3,"score":0.5471094250679016},{"id":"https://openalex.org/C2778220771","wikidata":"https://www.wikidata.org/wiki/Q1522579","display_name":"Substitution (logic)","level":2,"score":0.48321568965911865},{"id":"https://openalex.org/C2777965246","wikidata":"https://www.wikidata.org/wiki/Q899587","display_name":"Electrophilic substitution","level":2,"score":0.4709411859512329},{"id":"https://openalex.org/C111185830","wikidata":"https://www.wikidata.org/wiki/Q503396","display_name":"Substitution reaction","level":2,"score":0.45177099108695984},{"id":"https://openalex.org/C5304478","wikidata":"https://www.wikidata.org/wiki/Q502457","display_name":"Silylation","level":3,"score":0.41997990012168884},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.2535722851753235},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.14921075105667114},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.13718125224113464},{"id":"https://openalex.org/C145148216","wikidata":"https://www.wikidata.org/wiki/Q36496","display_name":"Ion","level":2,"score":0.0},{"id":"https://openalex.org/C41008148","wikidata":"https://www.wikidata.org/wiki/Q21198","display_name":"Computer science","level":0,"score":0.0},{"id":"https://openalex.org/C199360897","wikidata":"https://www.wikidata.org/wiki/Q9143","display_name":"Programming language","level":1,"score":0.0}],"mesh":[],"locations_count":1,"locations":[{"id":"doi:10.1021/ja9910560","doi":"https://doi.org/10.1021/ja9910560","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja9910560","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":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":25,"referenced_works":["https://openalex.org/W1963743624","https://openalex.org/W1967814169","https://openalex.org/W1971462175","https://openalex.org/W1971941360","https://openalex.org/W1976739017","https://openalex.org/W1990542316","https://openalex.org/W2012064842","https://openalex.org/W2012435897","https://openalex.org/W2015146930","https://openalex.org/W2020597653","https://openalex.org/W2023874741","https://openalex.org/W2025422035","https://openalex.org/W2030314990","https://openalex.org/W2035758827","https://openalex.org/W2061727172","https://openalex.org/W2078945255","https://openalex.org/W2139881842","https://openalex.org/W2152073966","https://openalex.org/W2949248221","https://openalex.org/W2949402375","https://openalex.org/W2951098702","https://openalex.org/W2951779478","https://openalex.org/W2952597193","https://openalex.org/W2952794327","https://openalex.org/W3005425261"],"related_works":["https://openalex.org/W2015146930","https://openalex.org/W2086290595","https://openalex.org/W2156064999","https://openalex.org/W1971462175","https://openalex.org/W4244400274","https://openalex.org/W2012435897","https://openalex.org/W2045248298","https://openalex.org/W2949402375","https://openalex.org/W2951504603","https://openalex.org/W2953351054"],"abstract_inverted_index":{"The":[0,25,58,90,114],"reaction":[1],"pathways":[2,123],"for":[3,135],"the":[4,29,94,132,148],"highly":[5],"enantioselective,":[6],"(\u2212)-sparteine-mediated,":[7],"lithiation\u2212substitution":[8],"reactions":[9,140],"of":[10,28,98,121,131,138,144],"N":[11,13],"-Boc-":[12],"-(":[14],"p":[15],"-methoxyphenyl)cinnamylamine":[16],"((":[17],"E":[18,100],")-":[19,101],"2":[20,102],")":[21],"have":[22],"been":[23,34],"investigated.":[24],"solution":[26],"structure":[27],"major":[30],"allyllithium":[31],"intermediate":[32],"has":[33],"determined":[35],"by":[36],"6":[37],"Li":[38],"and":[39,74,141],"13":[40],"C":[41],"NMR":[42],"to":[43,85],"be":[44,86,125],"a":[45],"monomeric":[46],"\u03b7":[47],"3":[48],"species,":[49],"endo":[50,67],"-":[51,53,55,61,63,65,68,70,72,76,78,80],"syn":[52,62,69,71,77,79],"anti":[54,64],"8\u00b71":[56,81],".":[57],"complexes":[59],"exo":[60,75],"8\u00b71,":[66,73],"are":[82],"also":[83],"shown":[84],"present":[87],"in":[88,93],"solution.":[89],"enantiodetermining":[91],"step":[92,137],"lithiation\u2212silylation":[95],"or":[96,110],"lithiation\u2212alkylation":[97],"(":[99],"can":[103,124],"involve":[104],"asymmetric":[105],"deprotonation,":[106],"dynamic":[107,111],"kinetic":[108],"resolution,":[109],"thermodynamic":[112],"resolution.":[113],"results":[115],"reported":[116],"herein":[117],"establish":[118],"that":[119],"each":[120,136],"these":[122,139],"operative.":[126],"This":[127],"information":[128],"allows":[129],"determination":[130],"stereochemical":[133],"course":[134],"permits":[142],"preparation":[143],"either":[145],"epimer":[146],"at":[147],"new":[149],"stereogenic":[150],"carbon.":[151]},"counts_by_year":[{"year":2025,"cited_by_count":1},{"year":2020,"cited_by_count":1},{"year":2019,"cited_by_count":2},{"year":2017,"cited_by_count":2},{"year":2016,"cited_by_count":1},{"year":2014,"cited_by_count":3},{"year":2012,"cited_by_count":2}],"updated_date":"2026-09-22T06:50:58.402377","created_date":"2016-06-24T00:00:00"}