{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,13]],"date-time":"2026-05-13T20:20:27Z","timestamp":1778703627112,"version":"3.51.4"},"reference-count":68,"publisher":"Wiley","issue":"24","license":[{"start":{"date-parts":[[2020,6,15]],"date-time":"2020-06-15T00:00:00Z","timestamp":1592179200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["SFRH\/BPD\/92394\/2013"],"award-info":[{"award-number":["SFRH\/BPD\/92394\/2013"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Eur J Org Chem"],"published-print":{"date-parts":[[2020,6,30]]},"abstract":"<jats:p>A one\u2010step, three\u2010component Petasis reaction of isatin derived 5\u2010arylboronate\u20103\u2010substituted oxindole derivatives with salicylaldehydes and secondary amines affords new enantiomerically pure structurally diverse 5\u2010\u03b1\u2010(3\u2010substituted\u2010oxindole)\u2010benzylamine derivatives. The reaction shows good substrate and reagent scope affording the products with good to excellent yields (up to &gt;99\u2009% yield) and enantioselectivities (up to 99\u2009% ee) using cheap and readily available (<jats:italic>R<\/jats:italic>)\u2010BINOL as the organocatalyst. A diastereoselective version of the reaction was also developed where moderate yields (37 to 55\u2009% yield), excellent enantioselectivities (up to 99\u2009% ee) and good diastereoselectivities (up to 86\u2009% de) were obtained for new 5\u2010\u03b1\u2010(3\u2010hydroxy\u2010oxindole)\u2010benzylamine derivatives, having two stereocenters. The reaction is also feasible on gram\u2010scale.<\/jats:p>","DOI":"10.1002\/ejoc.202000334","type":"journal-article","created":{"date-parts":[[2020,5,26]],"date-time":"2020-05-26T02:59:57Z","timestamp":1590461997000},"page":"3622-3634","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":17,"title":["Accessing New 5\u2010\u03b1\u2010(3,3\u2010Disubstituted Oxindole)\u2010Benzylamine Derivatives from Isatin: Stereoselective Organocatalytic Three Component Petasis Reaction"],"prefix":"10.1002","volume":"2020","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-1697-7871","authenticated-orcid":false,"given":"Carolina S.","family":"Marques","sequence":"first","affiliation":[{"name":"LAQV\u2010REQUIMTE University of \u00c9vora Institute for Research and Advanced Studies  Rua Rom\u00e3o Ramalho, 59 7000\u2010671 \u00c9vora Portugal"}]},{"given":"Patrick","family":"McArdle","sequence":"additional","affiliation":[{"name":"School of Chemistry National University of Ireland  Galway Ireland"}]},{"given":"Andrea","family":"Erxleben","sequence":"additional","affiliation":[{"name":"School of Chemistry National University of Ireland  Galway Ireland"}]},{"given":"Anthony J.","family":"Burke","sequence":"additional","affiliation":[{"name":"LAQV\u2010REQUIMTE University of \u00c9vora Institute for Research and Advanced Studies  Rua Rom\u00e3o Ramalho, 59 7000\u2010671 \u00c9vora Portugal"},{"name":"Chemistry Department School of Science and Technology University of \u00c9vora  Rua Rom\u00e3o Ramalho 59 7000\u2010671 \u00c9vora Portugal"}]}],"member":"311","published-online":{"date-parts":[[2020,6,15]]},"reference":[{"key":"e_1_2_6_2_1","volume-title":"Multicomponent Reactions in Organic Synthesis","author":"Zhu J.","year":"2015"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ddtec.2012.10.012"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200802140"},{"key":"e_1_2_6_3_3","doi-asserted-by":"publisher","DOI":"10.1021\/cr100233r"},{"key":"e_1_2_6_3_4","doi-asserted-by":"publisher","DOI":"10.1021\/acsmedchemlett.8b00579"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198107621"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19810930906"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(98)01484-1"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0028-1083239"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/9783527807253"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)61625-8"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja963178n"},{"key":"e_1_2_6_8_3","doi-asserted-by":"publisher","DOI":"10.1021\/ja981075u"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr100108k"},{"key":"e_1_2_6_9_2","first-page":"211","volume":"83","author":"Pyne S. G.","year":"2014","journal-title":"Org. React"},{"key":"e_1_2_6_9_3","doi-asserted-by":"publisher","DOI":"10.1016\/j.ddtec.2018.06.010"},{"key":"e_1_2_6_9_4","first-page":"275","volume-title":"ACS Symposium Series","author":"Guerrera C. A.","year":"2016"},{"key":"e_1_2_6_9_5","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.9b00214"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2cs15361k"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja8018934"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201103271"},{"key":"e_1_2_6_11_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201103271"},{"key":"e_1_2_6_11_4","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201611332"},{"key":"e_1_2_6_11_5","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201611332"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol203109a"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2012.11.043"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5RA00404G"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201501399"},{"key":"e_1_2_6_13_3","doi-asserted-by":"publisher","DOI":"10.1002\/cctc.201600901"},{"key":"e_1_2_6_13_4","doi-asserted-by":"publisher","DOI":"10.1055\/s-0036-1590940"},{"key":"e_1_2_6_13_5","doi-asserted-by":"publisher","DOI":"10.1002\/slct.201802889"},{"key":"e_1_2_6_13_6","unstructured":"f)A. J.Burke C. S.Marques D.Peixoto H.Viana A.Goth WO2015033261 2015."},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2016.05.004"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/slct.201600932"},{"key":"e_1_2_6_14_3","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2020.103753"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2018.01.025"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2017.04.002"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201700581"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201700581"},{"key":"e_1_2_6_16_3","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b00721"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2015.03.105"},{"key":"e_1_2_6_18_1","doi-asserted-by":"publisher","DOI":"10.1002\/3527606548"},{"key":"e_1_2_6_18_2","volume-title":"Catalytic Arylation Methods: From the Academic Lab to Industrial Processes","author":"Burke A. J.","year":"2015"},{"key":"e_1_2_6_18_3","doi-asserted-by":"publisher","DOI":"10.1021\/jo4013942"},{"key":"e_1_2_6_18_4","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2005.09.060"},{"key":"e_1_2_6_18_5","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(02)01265-0"},{"key":"e_1_2_6_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00128a024"},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo202117u"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)02014-1"},{"key":"e_1_2_6_21_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8RA08165D"},{"key":"e_1_2_6_22_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules23092317"},{"key":"e_1_2_6_23_1","volume-title":"Handbook of Reagents for Organic Synthesis: Reagents for Organocatalysis","author":"Rovis T.","year":"2016"},{"key":"e_1_2_6_24_1","doi-asserted-by":"publisher","DOI":"10.1021\/op060155c"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.201100780"},{"key":"e_1_2_6_25_1","unstructured":"Deposition Number 1959975 contains the supplementary crystallographic data for compound (4aaa). These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures servicewww.ccdc.cam.ac.uk\/structures."},{"key":"e_1_2_6_26_1","volume-title":"Purification of Laboratory Chemicals","author":"Amarego W. L. F.","year":"1996"},{"key":"e_1_2_6_27_1","doi-asserted-by":"publisher","DOI":"10.1002\/cmdc.201600266"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2015.09.125"},{"key":"e_1_2_6_27_3","doi-asserted-by":"publisher","DOI":"10.1039\/C8CC03962C"},{"key":"e_1_2_6_27_4","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b01827"},{"key":"e_1_2_6_27_5","doi-asserted-by":"publisher","DOI":"10.1021\/jm900286j"},{"key":"e_1_2_6_27_6","doi-asserted-by":"publisher","DOI":"10.1055\/s-2001-12776"},{"key":"e_1_2_6_27_7","doi-asserted-by":"publisher","DOI":"10.1016\/j.jorganchem.2007.02.034"},{"key":"e_1_2_6_27_8","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2012.09.036"},{"key":"e_1_2_6_27_9","doi-asserted-by":"publisher","DOI":"10.1021\/acs.organomet.6b00477"},{"key":"e_1_2_6_27_10","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2018.03.039"},{"key":"e_1_2_6_27_11","doi-asserted-by":"publisher","DOI":"10.1055\/s-0037-1610537"},{"key":"e_1_2_6_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo800727s"}],"container-title":["European Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fejoc.202000334","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/ejoc.202000334","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/ejoc.202000334","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/ejoc.202000334","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,15]],"date-time":"2025-10-15T11:37:44Z","timestamp":1760528264000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/ejoc.202000334"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,6,15]]},"references-count":68,"journal-issue":{"issue":"24","published-print":{"date-parts":[[2020,6,30]]}},"alternative-id":["10.1002\/ejoc.202000334"],"URL":"https:\/\/doi.org\/10.1002\/ejoc.202000334","archive":["Portico"],"relation":{},"ISSN":["1434-193X","1099-0690"],"issn-type":[{"value":"1434-193X","type":"print"},{"value":"1099-0690","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,6,15]]},"assertion":[{"value":"2020-03-13","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2020-06-15","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}