{"id":"https://openalex.org/W1996259344","doi":"https://doi.org/10.1021/ja106593m","title":"Enantioselective \u03b1-Benzylation of Aldehydes via Photoredox Organocatalysis","display_name":"Enantioselective \u03b1-Benzylation of Aldehydes via Photoredox Organocatalysis","publication_year":2010,"publication_date":"2010-09-10","ids":{"openalex":"https://openalex.org/W1996259344","doi":"https://doi.org/10.1021/ja106593m","mag":"1996259344","pmid":"https://pubmed.ncbi.nlm.nih.gov/20831195","pmcid":"https://www.ncbi.nlm.nih.gov/pmc/articles/3056320"},"language":"en","primary_location":{"id":"doi:10.1021/ja106593m","doi":"https://doi.org/10.1021/ja106593m","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja106593m","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/3056320","any_repository_has_fulltext":true},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5038454561","display_name":"Hui\u2010Wen Shih","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":"Hui-Wen Shih","raw_affiliation_strings":["Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544","Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, USA"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544","institution_ids":["https://openalex.org/I20089843"]},{"raw_affiliation_string":"Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, USA","institution_ids":["https://openalex.org/I20089843"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5042213090","display_name":"Mark N. Vander Wal","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":"Mark N. Vander Wal","raw_affiliation_strings":["Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544","institution_ids":["https://openalex.org/I20089843"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5032283415","display_name":"Rebecca L. Grange","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":"Rebecca L. Grange","raw_affiliation_strings":["Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Merck Center for Catalysis at 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 at Princeton University, Princeton, New Jersey 08544"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Merck Center for Catalysis at 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":27.3878,"has_fulltext":false,"cited_by_count":510,"citation_normalized_percentile":{"value":0.99933272,"is_in_top_1_percent":true,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":98,"max":100},"biblio":{"volume":"132","issue":"39","first_page":"13600","last_page":"13603"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10701","display_name":"Radical Photochemical Reactions","score":0.7846999764442444,"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/T10701","display_name":"Radical Photochemical Reactions","score":0.7846999764442444,"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":0.20250000059604645,"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":0.005400000140070915,"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"}}],"keywords":[{"id":"https://openalex.org/keywords/aldehydes","display_name":"aldehydes","score":0.9390000104904175},{"id":"https://openalex.org/keywords/fluorescent-lighting","display_name":"fluorescent lighting","score":0.6880000233650208},{"id":"https://openalex.org/keywords/angiogenesis-inhibition","display_name":"angiogenesis inhibition","score":0.9570000171661377}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9663341045379639},{"id":"https://openalex.org/C146686406","wikidata":"https://www.wikidata.org/wiki/Q898628","display_name":"Enantioselective synthesis","level":3,"score":0.9259070158004761},{"id":"https://openalex.org/C66972969","wikidata":"https://www.wikidata.org/wiki/Q898995","display_name":"Organocatalysis","level":4,"score":0.7450684309005737},{"id":"https://openalex.org/C2779825165","wikidata":"https://www.wikidata.org/wiki/Q101497","display_name":"Aldehyde","level":3,"score":0.6870236992835999},{"id":"https://openalex.org/C2781076698","wikidata":"https://www.wikidata.org/wiki/Q718074","display_name":"Aryl","level":3,"score":0.6237952709197998},{"id":"https://openalex.org/C134121241","wikidata":"https://www.wikidata.org/wiki/Q899301","display_name":"Yield (engineering)","level":2,"score":0.586845874786377},{"id":"https://openalex.org/C45849291","wikidata":"https://www.wikidata.org/wiki/Q17166058","display_name":"Photoredox catalysis","level":4,"score":0.5518336296081543},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.5384137034416199},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.4880884885787964},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.4858776926994324},{"id":"https://openalex.org/C528581852","wikidata":"https://www.wikidata.org/wiki/Q877","display_name":"Iridium","level":3,"score":0.42763036489486694},{"id":"https://openalex.org/C65165184","wikidata":"https://www.wikidata.org/wiki/Q218831","display_name":"Photocatalysis","level":3,"score":0.22023499011993408},{"id":"https://openalex.org/C2780263894","wikidata":"https://www.wikidata.org/wiki/Q335268","display_name":"Alkyl","level":2,"score":0.0},{"id":"https://openalex.org/C192562407","wikidata":"https://www.wikidata.org/wiki/Q228736","display_name":"Materials science","level":0,"score":0.0},{"id":"https://openalex.org/C191897082","wikidata":"https://www.wikidata.org/wiki/Q11467","display_name":"Metallurgy","level":1,"score":0.0}],"mesh":[{"descriptor_ui":"D000447","descriptor_name":"Aldehydes","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D000447","descriptor_name":"Aldehydes","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":"D007495","descriptor_name":"Iridium","qualifier_ui":"Q000737","qualifier_name":"chemistry","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":"D010777","descriptor_name":"Photochemistry","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},{"descriptor_ui":"D018360","descriptor_name":"Crystallography, X-Ray","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D048289","descriptor_name":"Imidazolidines","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true}],"locations_count":3,"locations":[{"id":"doi:10.1021/ja106593m","doi":"https://doi.org/10.1021/ja106593m","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja106593m","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:20831195","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/20831195","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:pubmedcentral.nih.gov:3056320","doi":null,"is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/3056320","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:pubmedcentral.nih.gov:3056320","doi":null,"is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/3056320","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"},"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G3882020948","display_name":"New Strategies in Metallaphotoredox Catalysis","funder_award_id":"R01GM093213","funder_id":"https://openalex.org/F4320337354","funder_display_name":"National Institute of General Medical Sciences"},{"id":"https://openalex.org/G7747101108","display_name":null,"funder_award_id":"R01 01 GM093213-01","funder_id":"https://openalex.org/F4320337354","funder_display_name":"National Institute of General Medical Sciences"}],"funders":[{"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":36,"referenced_works":["https://openalex.org/W142358202","https://openalex.org/W207396953","https://openalex.org/W1562923576","https://openalex.org/W1985066293","https://openalex.org/W1994179009","https://openalex.org/W1999031172","https://openalex.org/W1999601844","https://openalex.org/W1999797029","https://openalex.org/W2007683040","https://openalex.org/W2014971180","https://openalex.org/W2018458872","https://openalex.org/W2023438873","https://openalex.org/W2029253088","https://openalex.org/W2044975448","https://openalex.org/W2046754996","https://openalex.org/W2049917615","https://openalex.org/W2051419557","https://openalex.org/W2051822378","https://openalex.org/W2063283966","https://openalex.org/W2073250189","https://openalex.org/W2079822650","https://openalex.org/W2083002268","https://openalex.org/W2085712428","https://openalex.org/W2087152379","https://openalex.org/W2089553882","https://openalex.org/W2089943991","https://openalex.org/W2094129737","https://openalex.org/W2099798519","https://openalex.org/W2116665648","https://openalex.org/W2149983834","https://openalex.org/W2153893686","https://openalex.org/W2155604981","https://openalex.org/W2329763538","https://openalex.org/W2950485537","https://openalex.org/W2951782980","https://openalex.org/W3005470321"],"related_works":["https://openalex.org/W2951135813","https://openalex.org/W2587464474","https://openalex.org/W2051822378","https://openalex.org/W4238979691","https://openalex.org/W2554771887","https://openalex.org/W3045894727","https://openalex.org/W2661054184","https://openalex.org/W2130871639","https://openalex.org/W2738990824","https://openalex.org/W2405374401"],"abstract_inverted_index":{"The":[0,14,49],"first":[1],"enantioselective":[2],"aldehyde":[3],"\u03b1-benzylation":[4],"using":[5],"electron-deficient":[6],"aryl":[7],"and":[8,22,47],"heteroaryl":[9],"substrates":[10],"has":[11,54],"been":[12,55],"accomplished.":[13],"productive":[15],"merger":[16],"of":[17,32,51],"a":[18,23],"chiral":[19],"imidazolidinone":[20],"organocatalyst":[21],"commercially":[24],"available":[25],"iridium":[26],"photoredox":[27],"catalyst":[28],"in":[29,42],"the":[30,38],"presence":[31],"household":[33],"fluorescent":[34],"light":[35],"directly":[36],"affords":[37],"desired":[39],"homobenzylic":[40],"stereogenicity":[41],"good":[43],"to":[44,60],"excellent":[45],"yield":[46],"enantioselectivity.":[48],"utility":[50],"this":[52],"methodology":[53],"demonstrated":[56],"via":[57],"rapid":[58],"access":[59],"an":[61],"enantioenriched":[62],"drug":[63],"target":[64],"for":[65],"angiogenesis":[66],"suppression.":[67]},"counts_by_year":[{"year":2026,"cited_by_count":6},{"year":2025,"cited_by_count":6},{"year":2024,"cited_by_count":12},{"year":2023,"cited_by_count":12},{"year":2022,"cited_by_count":24},{"year":2021,"cited_by_count":28},{"year":2020,"cited_by_count":22},{"year":2019,"cited_by_count":29},{"year":2018,"cited_by_count":31},{"year":2017,"cited_by_count":31},{"year":2016,"cited_by_count":38},{"year":2015,"cited_by_count":48},{"year":2014,"cited_by_count":50},{"year":2013,"cited_by_count":52},{"year":2012,"cited_by_count":69}],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2016-06-24T00:00:00"}
