{"id":"https://openalex.org/W2010768957","doi":"https://doi.org/10.1021/ja053270w","title":"Asymmetric Synthesis of 3,3-Diarylpropanals with Chiral Diene\u2212Rhodium Catalysts","display_name":"Asymmetric Synthesis of 3,3-Diarylpropanals with Chiral Diene\u2212Rhodium Catalysts","publication_year":2005,"publication_date":"2005-07-14","ids":{"openalex":"https://openalex.org/W2010768957","doi":"https://doi.org/10.1021/ja053270w","mag":"2010768957","pmid":"https://pubmed.ncbi.nlm.nih.gov/16076189"},"language":"en","primary_location":{"id":"doi:10.1021/ja053270w","doi":"https://doi.org/10.1021/ja053270w","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja053270w","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":false,"oa_status":"closed","oa_url":null,"any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5089379813","display_name":"Jean\u2010Fran\u00e7ois Paquin","orcid":"https://orcid.org/0000-0003-2412-3083","observed_orcids":["https://orcid.org/0000-0003-2412-3083"]},"institutions":[{"id":"https://openalex.org/I35440088","display_name":"ETH Zurich","ror":"https://ror.org/05a28rw58","country_code":"CH","type":"education","lineage":["https://openalex.org/I2799323385","https://openalex.org/I35440088"]},{"id":"https://openalex.org/I4405255184","display_name":"Laboratory of Organic Chemistry","ror":"https://ror.org/02q73ep21","country_code":"CH","type":"facility","lineage":["https://openalex.org/I2799323385","https://openalex.org/I35440088","https://openalex.org/I4405255184"]}],"countries":["CH"],"is_corresponding":false,"raw_author_name":"Jean-Fran\u00e7ois Paquin","raw_affiliation_strings":["Laboratorium f\u00fcr Organische Chemie, ETH H\u00f6nggerberg, CH-8093 Z\u00fcrich, Switzerland"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Laboratorium f\u00fcr Organische Chemie, ETH H\u00f6nggerberg, CH-8093 Z\u00fcrich, Switzerland","institution_ids":["https://openalex.org/I35440088","https://openalex.org/I4405255184"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5040857510","display_name":"Christian Defieber","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I35440088","display_name":"ETH Zurich","ror":"https://ror.org/05a28rw58","country_code":"CH","type":"education","lineage":["https://openalex.org/I2799323385","https://openalex.org/I35440088"]},{"id":"https://openalex.org/I4405255184","display_name":"Laboratory of Organic Chemistry","ror":"https://ror.org/02q73ep21","country_code":"CH","type":"facility","lineage":["https://openalex.org/I2799323385","https://openalex.org/I35440088","https://openalex.org/I4405255184"]}],"countries":["CH"],"is_corresponding":false,"raw_author_name":"Christian Defieber","raw_affiliation_strings":["Laboratorium f\u00fcr Organische Chemie, ETH H\u00f6nggerberg, CH-8093 Z\u00fcrich, Switzerland"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Laboratorium f\u00fcr Organische Chemie, ETH H\u00f6nggerberg, CH-8093 Z\u00fcrich, Switzerland","institution_ids":["https://openalex.org/I35440088","https://openalex.org/I4405255184"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5036992723","display_name":"Corey R. J. Stephenson","orcid":"https://orcid.org/0000-0002-2443-5514","observed_orcids":["https://orcid.org/0000-0002-2443-5514"]},"institutions":[{"id":"https://openalex.org/I35440088","display_name":"ETH Zurich","ror":"https://ror.org/05a28rw58","country_code":"CH","type":"education","lineage":["https://openalex.org/I2799323385","https://openalex.org/I35440088"]},{"id":"https://openalex.org/I4405255184","display_name":"Laboratory of Organic Chemistry","ror":"https://ror.org/02q73ep21","country_code":"CH","type":"facility","lineage":["https://openalex.org/I2799323385","https://openalex.org/I35440088","https://openalex.org/I4405255184"]}],"countries":["CH"],"is_corresponding":false,"raw_author_name":"Corey R. J. Stephenson","raw_affiliation_strings":["Laboratorium f\u00fcr Organische Chemie, ETH H\u00f6nggerberg, CH-8093 Z\u00fcrich, Switzerland"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Laboratorium f\u00fcr Organische Chemie, ETH H\u00f6nggerberg, CH-8093 Z\u00fcrich, Switzerland","institution_ids":["https://openalex.org/I35440088","https://openalex.org/I4405255184"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5036732266","display_name":"Erick M. Carreira","orcid":"https://orcid.org/0000-0003-1472-490X","observed_orcids":["https://orcid.org/0000-0003-1472-490X"]},"institutions":[{"id":"https://openalex.org/I35440088","display_name":"ETH Zurich","ror":"https://ror.org/05a28rw58","country_code":"CH","type":"education","lineage":["https://openalex.org/I2799323385","https://openalex.org/I35440088"]},{"id":"https://openalex.org/I4405255184","display_name":"Laboratory of Organic Chemistry","ror":"https://ror.org/02q73ep21","country_code":"CH","type":"facility","lineage":["https://openalex.org/I2799323385","https://openalex.org/I35440088","https://openalex.org/I4405255184"]}],"countries":["CH"],"is_corresponding":false,"raw_author_name":"Erick M. Carreira","raw_affiliation_strings":["Laboratorium f\u00fcr Organische Chemie, ETH H\u00f6nggerberg, CH-8093 Z\u00fcrich, Switzerland"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Laboratorium f\u00fcr Organische Chemie, ETH H\u00f6nggerberg, CH-8093 Z\u00fcrich, Switzerland","institution_ids":["https://openalex.org/I35440088","https://openalex.org/I4405255184"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":2,"corresponding_author_ids":[],"corresponding_institution_ids":[],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":12.9567,"has_fulltext":false,"cited_by_count":275,"citation_normalized_percentile":{"value":0.99532937,"is_in_top_1_percent":true,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":94,"max":100},"biblio":{"volume":"127","issue":"31","first_page":"10850","last_page":"10851"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10013","display_name":"Asymmetric Synthesis and Catalysis","score":0.9932000041007996,"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":0.9932000041007996,"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/T10548","display_name":"Catalytic Cross-Coupling Reactions","score":0.0031999999191612005,"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":0.0012000000569969416,"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/asymmetric-synthesis","display_name":"asymmetric synthesis","score":0.8529999852180481},{"id":"https://openalex.org/keywords/arylboronic-acids","display_name":"arylboronic acids","score":0.9810000061988831},{"id":"https://openalex.org/keywords/cinnamaldehyde-derivatives","display_name":"cinnamaldehyde derivatives","score":0.9800000190734863},{"id":"https://openalex.org/keywords/enantioselective-addition","display_name":"enantioselective addition","score":0.7429999709129333},{"id":"https://openalex.org/keywords/alpha-beta-unsaturated-aldehydes","display_name":"\u03b1,\u03b2-unsaturated aldehydes","score":0.5550000071525574},{"id":"https://openalex.org/keywords/chiral-building-blocks","display_name":"chiral building blocks","score":0.5320000052452087}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9675772190093994},{"id":"https://openalex.org/C2778733088","wikidata":"https://www.wikidata.org/wiki/Q192678","display_name":"Diene","level":3,"score":0.8766334056854248},{"id":"https://openalex.org/C521398313","wikidata":"https://www.wikidata.org/wiki/Q1087","display_name":"Rhodium","level":3,"score":0.8717441558837891},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.7125537991523743},{"id":"https://openalex.org/C146686406","wikidata":"https://www.wikidata.org/wiki/Q898628","display_name":"Enantioselective synthesis","level":3,"score":0.5588250160217285},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.42938101291656494},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.4020422101020813},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.32225725054740906},{"id":"https://openalex.org/C176933379","wikidata":"https://www.wikidata.org/wiki/Q131877","display_name":"Natural rubber","level":2,"score":0.0}],"mesh":[],"locations_count":2,"locations":[{"id":"doi:10.1021/ja053270w","doi":"https://doi.org/10.1021/ja053270w","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja053270w","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:16076189","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/16076189","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"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":22,"referenced_works":["https://openalex.org/W1971530787","https://openalex.org/W1979178590","https://openalex.org/W2009557533","https://openalex.org/W2019862779","https://openalex.org/W2021508376","https://openalex.org/W2036557488","https://openalex.org/W2040599187","https://openalex.org/W2047176101","https://openalex.org/W2052732960","https://openalex.org/W2074204990","https://openalex.org/W2080795224","https://openalex.org/W2081318694","https://openalex.org/W2098941592","https://openalex.org/W2105408970","https://openalex.org/W2123150858","https://openalex.org/W2123261020","https://openalex.org/W2146161559","https://openalex.org/W2153123409","https://openalex.org/W2170080608","https://openalex.org/W2952449773","https://openalex.org/W2953269131","https://openalex.org/W3193096982"],"related_works":["https://openalex.org/W2155654405","https://openalex.org/W2315804413","https://openalex.org/W2061101019","https://openalex.org/W2126401783","https://openalex.org/W2099850064","https://openalex.org/W2001554056","https://openalex.org/W2952447711","https://openalex.org/W2115187760","https://openalex.org/W2070499812","https://openalex.org/W2017124847"],"abstract_inverted_index":{"A":[0],"general":[1],"route":[2],"to":[3,23],"enantioenriched":[4],"3,3-diarylpropanals":[5],"is":[6],"presented.":[7],"These":[8],"useful":[9],"building":[10],"blocks":[11],"are":[12],"prepared":[13],"via":[14],"an":[15],"asymmetric":[16],"rhodium-catalyzed":[17],"conjugate":[18],"addition":[19,33],"of":[20,29,34],"arylboronic":[21],"acids":[22,42],"cinnamaldehyde":[24],"derivatives":[25],"in":[26,48],"the":[27],"presence":[28],"chiral":[30],"dienes.":[31],"The":[32],"both":[35],"electron-poor":[36],"as":[37,39],"well":[38],"electron-rich":[40],"boronic":[41],"proceeds":[43],"smoothly":[44],"with":[45,51],"various":[46],"enals":[47],"63-90%":[49],"yield":[50],"high":[52],"enantioselectivities":[53],"(89-93%":[54],"ee).":[55]},"counts_by_year":[{"year":2026,"cited_by_count":5},{"year":2025,"cited_by_count":4},{"year":2024,"cited_by_count":2},{"year":2023,"cited_by_count":4},{"year":2022,"cited_by_count":4},{"year":2021,"cited_by_count":8},{"year":2020,"cited_by_count":5},{"year":2019,"cited_by_count":11},{"year":2018,"cited_by_count":7},{"year":2017,"cited_by_count":12},{"year":2016,"cited_by_count":13},{"year":2015,"cited_by_count":11},{"year":2014,"cited_by_count":18},{"year":2013,"cited_by_count":13},{"year":2012,"cited_by_count":18}],"updated_date":"2026-08-21T09:56:20.448147","created_date":"2016-06-24T00:00:00"}