{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,29]],"date-time":"2026-04-29T21:03:47Z","timestamp":1777496627355,"version":"3.51.4"},"reference-count":41,"publisher":"Wiley","issue":"1","license":[{"start":{"date-parts":[[2020,11,24]],"date-time":"2020-11-24T00:00:00Z","timestamp":1606176000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100003141","name":"Consejo Nacional de Ciencia y Tecnolog\u00eda","doi-asserted-by":"publisher","award":["290754"],"award-info":[{"award-number":["290754"]}],"id":[{"id":"10.13039\/501100003141","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003141","name":"Consejo Nacional de Ciencia y Tecnolog\u00eda","doi-asserted-by":"publisher","award":["170296"],"award-info":[{"award-number":["170296"]}],"id":[{"id":"10.13039\/501100003141","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003141","name":"Consejo Nacional de Ciencia y Tecnolog\u00eda","doi-asserted-by":"publisher","award":["286620"],"award-info":[{"award-number":["286620"]}],"id":[{"id":"10.13039\/501100003141","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chirality"],"published-print":{"date-parts":[[2021,1]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>In this study, the novel bifunctional homochiral thiourea\u2010<jats:italic>L<\/jats:italic>\u2010prolinamides <jats:bold>1\u20134<\/jats:bold>, tertiary amino<jats:italic>\u2010L<\/jats:italic>\u2010prolinamide <jats:bold>5<\/jats:bold>, and bis\u2010<jats:italic>L<\/jats:italic>\u2010prolinamides <jats:bold>6<\/jats:bold> and <jats:bold>7<\/jats:bold> were prepared from enantiomerically pure (11<jats:italic>R<\/jats:italic>,12<jats:italic>R<\/jats:italic>)\u201011,12\u2010diamino\u20109,10\u2010dihydro\u20109,10\u2010ethanoanthracene <jats:bold>8<\/jats:bold> and (11<jats:italic>S<\/jats:italic>,12<jats:italic>S<\/jats:italic>)\u201011,12\u2010diamino\u20109,10\u2010dihydro\u20109,10\u2010ethanoanthracene <jats:bold><jats:italic>ent<\/jats:italic>\u20108<\/jats:bold>. Highly enantioselective and diastereoselective aldolic intermolecular reactions (up to 95% enantiomeric excess<jats:italic>,<\/jats:italic> 93:7 <jats:italic>anti<\/jats:italic>\/<jats:italic>syn<\/jats:italic>) between aliphatic ketones (20 equiv) and a range of aromatic aldehydes (1 equiv) were successfully carried out in the presence of water (10 equiv) and monochloroacetic acid (10 mol%), solvent\u2010free conditions, at room temperature over 24 h using organocatalysts <jats:bold>1\u20137<\/jats:bold> (5 mol%). Stereoselective induction using density functional theory\u2013based methods was consistent with the experimental data.<\/jats:p>","DOI":"10.1002\/chir.23283","type":"journal-article","created":{"date-parts":[[2020,11,25]],"date-time":"2020-11-25T05:36:43Z","timestamp":1606282603000},"page":"22-36","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Homochiral bifunctional <i>L<\/i>\u2010prolinamide\u2010 and <i>L\u2010<\/i>bis\u2010prolinamide\u2010catalyzed asymmetric aldol reactions performed in wet solvent\u2010free conditions"],"prefix":"10.1002","volume":"33","author":[{"given":"Gabriela","family":"Huelgas","sequence":"first","affiliation":[{"name":"Departamento de Ciencias Qu\u00edmico Biol\u00f3gicas Universidad de las Americas Puebla  Cholula Puebla Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1220-082X","authenticated-orcid":false,"given":"Ratnasamy","family":"Somanathan","sequence":"additional","affiliation":[{"name":"Centro de Graduados e Investigaci\u00f3n en Qu\u00edmica Tecnol\u00f3gico Nacional de M\u00e9xico\/Instituto Tecnol\u00f3gico de Tijuana  Tijuana Baja California Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Julio M.","family":"Hern\u00e1ndez P\u00e9rez","sequence":"additional","affiliation":[{"name":"Facultad de Ciencias Qu\u00edmicas Benem\u00e9rita Universidad Aut\u00f3noma de Puebla  Puebla Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Haydee","family":"Rojas Cabrera","sequence":"additional","affiliation":[{"name":"Departamento de Ciencias Qu\u00edmico Biol\u00f3gicas Universidad de las Americas Puebla  Cholula Puebla Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Maximiliano","family":"de la Higuera Mac\u00edas","sequence":"additional","affiliation":[{"name":"Departamento de Ciencias Qu\u00edmico Biol\u00f3gicas Universidad de las Americas Puebla  Cholula Puebla Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Alejandra","family":"Dom\u00ednguez\u2010Huerta","sequence":"additional","affiliation":[{"name":"Departamento de Ciencias Qu\u00edmico Biol\u00f3gicas Universidad de las Americas Puebla  Cholula Puebla Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Roc\u00edo","family":"Sabala","sequence":"additional","affiliation":[{"name":"Departamento de Ciencias Qu\u00edmico Biol\u00f3gicas Universidad de las Americas Puebla  Cholula Puebla Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5619-2513","authenticated-orcid":false,"given":"Cecilia","family":"Anaya de Parrodi","sequence":"additional","affiliation":[{"name":"Departamento de Ciencias Qu\u00edmico Biol\u00f3gicas Universidad de las Americas Puebla  Cholula Puebla Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2020,11,24]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7NJ04424K"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2018.07.016"},{"key":"e_1_2_8_4_1","first-page":"490","article-title":"Dual activation in organocatalysis: Design of tunable and bifunctional organocatalysts and their applications in enantioselective reactions","volume":"2012","author":"Lu L\u2010Q","year":"2012","journal-title":"Synlett"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00657"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201400035"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.2174\/138527212803520128"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200700363"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2011.06.042"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4RA02690J"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1039\/c0cc05224h"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.2174\/157017941205150821124901"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0030-1260029"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2016.01.011"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja994280y"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol202284n"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4RA03362K"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2ob25693b"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2012.08.023"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2011.05.008"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00925a003"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr0684016"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b00828"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2015.01.009"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2011.09.101"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2015.09.009"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja01491a036"},{"key":"e_1_2_8_28_1","first-page":"3196","article-title":"A convenient and scaleable synthesis of 11,12\u2010diamino\u20109,10\u2010dihydro\u20109,10\u2010ethanoanthracene and its enantiomers","volume":"2005","author":"Fox ME","year":"2005","journal-title":"Synthesis"},{"key":"e_1_2_8_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja0510156"},{"key":"e_1_2_8_30_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201901344"},{"key":"e_1_2_8_31_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3ob41403e"},{"key":"e_1_2_8_32_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201100707"},{"key":"e_1_2_8_33_1","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201500078"},{"key":"e_1_2_8_34_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3ob27250h"},{"key":"e_1_2_8_35_1","doi-asserted-by":"publisher","DOI":"10.1002\/tcr.201300040"},{"key":"e_1_2_8_36_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6OB00783J"},{"key":"e_1_2_8_37_1","doi-asserted-by":"publisher","DOI":"10.1039\/C3CS60202H"},{"key":"e_1_2_8_38_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6CS00239K"},{"key":"e_1_2_8_39_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00676"},{"key":"e_1_2_8_40_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2014.12.007"},{"key":"e_1_2_8_41_1","volume-title":"Gaussian 09. Revision D.01","author":"Frisch MJ","year":"2013"},{"key":"e_1_2_8_42_1","unstructured":"ZhurkoGA.Chemcraft \u2010 graphical program for visualization of quantum chemistry computations. Ivanovo Russia 2005.https:\/\/chemcraftprog.com"}],"container-title":["Chirality"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chir.23283","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chir.23283","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chir.23283","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,9,4]],"date-time":"2023-09-04T05:20:18Z","timestamp":1693804818000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/chir.23283"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,11,24]]},"references-count":41,"journal-issue":{"issue":"1","published-print":{"date-parts":[[2021,1]]}},"alternative-id":["10.1002\/chir.23283"],"URL":"https:\/\/doi.org\/10.1002\/chir.23283","archive":["Portico"],"relation":{},"ISSN":["0899-0042","1520-636X"],"issn-type":[{"value":"0899-0042","type":"print"},{"value":"1520-636X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,11,24]]},"assertion":[{"value":"2020-06-22","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2020-10-05","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2020-11-24","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}