{"id":"https://openalex.org/W2060210302","doi":"https://doi.org/10.1021/ja904504j","title":"Enantioselective Aldehyde \u03b1-Nitroalkylation via Oxidative Organocatalysis","display_name":"Enantioselective Aldehyde \u03b1-Nitroalkylation via Oxidative Organocatalysis","publication_year":2009,"publication_date":"2009-07-24","ids":{"openalex":"https://openalex.org/W2060210302","doi":"https://doi.org/10.1021/ja904504j","mag":"2060210302","pmid":"https://pubmed.ncbi.nlm.nih.gov/19627154","pmcid":"https://www.ncbi.nlm.nih.gov/pmc/articles/3259685"},"language":"en","primary_location":{"id":"doi:10.1021/ja904504j","doi":"https://doi.org/10.1021/ja904504j","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja904504j","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/3259685","any_repository_has_fulltext":true},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5086479392","display_name":"Jonathan E. Wilson","orcid":"https://orcid.org/0000-0002-7943-5861","observed_orcids":["https://orcid.org/0000-0002-7943-5861"]},"institutions":[{"id":"https://openalex.org/I20089843","display_name":"Princeton University","ror":"https://ror.org/00hx57361","country_code":"US","type":"education","lineage":["https://openalex.org/I20089843"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Jonathan E. Wilson","raw_affiliation_strings":["Merck Center for Catalysis, Princeton University, Princeton, New Jersey 08544","Merck Center for Catalysis, Princeton University, Princeton, New Jersey 08544, USA"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Merck Center for Catalysis, Princeton University, Princeton, New Jersey 08544","institution_ids":["https://openalex.org/I20089843"]},{"raw_affiliation_string":"Merck Center for Catalysis, Princeton University, Princeton, New Jersey 08544, USA","institution_ids":["https://openalex.org/I20089843"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5085571948","display_name":"Anthony D. Casarez","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I20089843","display_name":"Princeton University","ror":"https://ror.org/00hx57361","country_code":"US","type":"education","lineage":["https://openalex.org/I20089843"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Anthony D. Casarez","raw_affiliation_strings":["Merck Center for Catalysis, Princeton University, Princeton, New Jersey 08544"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Merck Center for Catalysis, Princeton University, Princeton, New Jersey 08544","institution_ids":["https://openalex.org/I20089843"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5025805979","display_name":"David W. C. MacMillan","orcid":"https://orcid.org/0000-0001-6447-0587","observed_orcids":["https://orcid.org/0000-0001-6447-0587"]},"institutions":[{"id":"https://openalex.org/I20089843","display_name":"Princeton University","ror":"https://ror.org/00hx57361","country_code":"US","type":"education","lineage":["https://openalex.org/I20089843"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"David W. C. MacMillan","raw_affiliation_strings":["Merck Center for Catalysis, Princeton University, Princeton, New Jersey 08544"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Merck Center for Catalysis, Princeton University, Princeton, New Jersey 08544","institution_ids":["https://openalex.org/I20089843"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":["https://openalex.org/A5025805979"],"corresponding_institution_ids":["https://openalex.org/I20089843"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":8.5352,"has_fulltext":false,"cited_by_count":128,"citation_normalized_percentile":{"value":0.98648623,"is_in_top_1_percent":false,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":93,"max":100},"biblio":{"volume":"131","issue":"32","first_page":"11332","last_page":"11334"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10013","display_name":"Asymmetric Synthesis and Catalysis","score":0.9937000274658203,"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":0.9937000274658203,"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":0.0010999999940395355,"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/T11831","display_name":"Chemical Synthesis and 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/asymmetric-organocatalysis","display_name":"asymmetric organocatalysis","score":0.9020000100135803},{"id":"https://openalex.org/keywords/oxidative-coupling","display_name":"oxidative coupling","score":0.8330000042915344},{"id":"https://openalex.org/keywords/enamine-intermediates","display_name":"enamine intermediates","score":0.7519999742507935},{"id":"https://openalex.org/keywords/silyl-nitronates","display_name":"silyl nitronates","score":0.9039999842643738},{"id":"https://openalex.org/keywords/beta-amino-acid-synthesis","display_name":"\u03b2-amino acid synthesis","score":0.7519999742507935}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9542686939239502},{"id":"https://openalex.org/C146686406","wikidata":"https://www.wikidata.org/wiki/Q898628","display_name":"Enantioselective synthesis","level":3,"score":0.905627965927124},{"id":"https://openalex.org/C2779825165","wikidata":"https://www.wikidata.org/wiki/Q101497","display_name":"Aldehyde","level":3,"score":0.8484944701194763},{"id":"https://openalex.org/C66972969","wikidata":"https://www.wikidata.org/wiki/Q898995","display_name":"Organocatalysis","level":4,"score":0.8060308694839478},{"id":"https://openalex.org/C2776378156","wikidata":"https://www.wikidata.org/wiki/Q408018","display_name":"Enamine","level":3,"score":0.7819949984550476},{"id":"https://openalex.org/C2776343937","wikidata":"https://www.wikidata.org/wiki/Q1919899","display_name":"Nitronate","level":4,"score":0.6826704144477844},{"id":"https://openalex.org/C5304478","wikidata":"https://www.wikidata.org/wiki/Q502457","display_name":"Silylation","level":3,"score":0.6424219608306885},{"id":"https://openalex.org/C57600042","wikidata":"https://www.wikidata.org/wiki/Q227564","display_name":"Oxidative phosphorylation","level":2,"score":0.5244972109794617},{"id":"https://openalex.org/C131779359","wikidata":"https://www.wikidata.org/wiki/Q471875","display_name":"Amine gas treating","level":2,"score":0.47321242094039917},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.42079275846481323},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.4162026345729828},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.345700204372406},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.04691517353057861},{"id":"https://openalex.org/C2780639532","wikidata":"https://www.wikidata.org/wiki/Q7041427","display_name":"Nitro","level":3,"score":0.0},{"id":"https://openalex.org/C2780263894","wikidata":"https://www.wikidata.org/wiki/Q335268","display_name":"Alkyl","level":2,"score":0.0}],"mesh":[{"descriptor_ui":"D000447","descriptor_name":"Aldehydes","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":false},{"descriptor_ui":"D000447","descriptor_name":"Aldehydes","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D000478","descriptor_name":"Alkylation","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D000588","descriptor_name":"Amines","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D000596","descriptor_name":"Amino Acids","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D000596","descriptor_name":"Amino Acids","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D002384","descriptor_name":"Catalysis","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D008958","descriptor_name":"Models, Molecular","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D010084","descriptor_name":"Oxidation-Reduction","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"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/ja904504j","doi":"https://doi.org/10.1021/ja904504j","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja904504j","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:19627154","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/19627154","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:2265855","doi":null,"is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/3259685","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:3259685","doi":null,"is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/3259685","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:2265855","doi":null,"is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/3259685","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/G1093573212","display_name":"Photoredox Catalysis Applications in Organometallics and Chemical Biology","funder_award_id":"2r01gm078201-13","funder_id":"https://openalex.org/F4320332161","funder_display_name":"National Institutes of Health"},{"id":"https://openalex.org/G1588828791","display_name":null,"funder_award_id":"R01-GM078201","funder_id":"https://openalex.org/F4320337354","funder_display_name":"National Institute of General Medical Sciences"},{"id":"https://openalex.org/G212192920","display_name":null,"funder_award_id":"R01-GM078201-01-01","funder_id":"https://openalex.org/F4320337354","funder_display_name":"National Institute of General Medical Sciences"}],"funders":[{"id":"https://openalex.org/F4320332161","display_name":"National Institutes of Health","ror":"https://ror.org/01cwqze88"},{"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":20,"referenced_works":["https://openalex.org/W626635725","https://openalex.org/W1566080486","https://openalex.org/W1968906096","https://openalex.org/W1983345629","https://openalex.org/W1983514663","https://openalex.org/W2016493151","https://openalex.org/W2020199022","https://openalex.org/W2045499543","https://openalex.org/W2063598218","https://openalex.org/W2074482386","https://openalex.org/W2077350653","https://openalex.org/W2092640890","https://openalex.org/W2129152184","https://openalex.org/W2146780243","https://openalex.org/W2167450591","https://openalex.org/W2325306093","https://openalex.org/W2330632487","https://openalex.org/W2478964621","https://openalex.org/W2951896462","https://openalex.org/W2972991031"],"related_works":["https://openalex.org/W1977457673","https://openalex.org/W2046809701","https://openalex.org/W2069134574","https://openalex.org/W2163196230","https://openalex.org/W4307340688","https://openalex.org/W2113788501","https://openalex.org/W2946126960","https://openalex.org/W2133438766","https://openalex.org/W2951796277","https://openalex.org/W2067491869"],"abstract_inverted_index":{"The":[0,10],"first":[1],"enantioselective":[2],"organocatalytic":[3],"alpha-nitroalkylation":[4],"of":[5,17,25,74,88],"aldehydes":[6],"has":[7],"been":[8,59],"accomplished.":[9],"aforementioned":[11],"process":[12],"involves":[13],"the":[14,45,55,86],"oxidative":[15],"coupling":[16],"an":[18,26,30],"enamine":[19],"intermediate,":[20],"generated":[21],"transiently":[22],"via":[23],"condensation":[24],"amine":[27],"catalyst":[28],"with":[29,32],"aldehyde,":[31],"a":[33,38,49,66,75,82],"silyl":[34,76],"nitronate":[35],"to":[36,54,64],"produce":[37],"beta-nitroaldehyde.":[39],"Two":[40],"methods,":[41],"one":[42],"that":[43,51,68],"furnishes":[44],"syn":[46],"beta-nitroaldehyde":[47],"and":[48,91],"second":[50],"provides":[52],"access":[53],"anti":[56],"isomer,":[57],"have":[58],"developed.":[60],"Data":[61],"are":[62],"presented":[63],"support":[65],"hypothesis":[67],"explains":[69],"this":[70],"phenomenon":[71],"in":[72,79],"terms":[73],"group-controlled":[77],"change":[78],"mechanism.":[80],"Finally,":[81],"three-step":[83],"procedure":[84],"for":[85],"synthesis":[87],"both":[89],"syn-":[90],"anti-alpha,beta-disubstituted":[92],"beta-amino":[93],"acids":[94],"is":[95],"presented.":[96]},"counts_by_year":[{"year":2026,"cited_by_count":2},{"year":2025,"cited_by_count":3},{"year":2024,"cited_by_count":5},{"year":2023,"cited_by_count":2},{"year":2022,"cited_by_count":3},{"year":2021,"cited_by_count":4},{"year":2020,"cited_by_count":2},{"year":2019,"cited_by_count":6},{"year":2018,"cited_by_count":7},{"year":2017,"cited_by_count":12},{"year":2016,"cited_by_count":3},{"year":2015,"cited_by_count":6},{"year":2014,"cited_by_count":9},{"year":2013,"cited_by_count":11},{"year":2012,"cited_by_count":14}],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2016-06-24T00:00:00"}
