{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,15]],"date-time":"2025-10-15T17:27:59Z","timestamp":1760549279713,"version":"build-2065373602"},"reference-count":86,"publisher":"Wiley","issue":"6","license":[{"start":{"date-parts":[[2012,11,30]],"date-time":"2012-11-30T00:00:00Z","timestamp":1354233600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2013,2,4]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A synthetic method that relies on NIS (<jats:italic>N<\/jats:italic>\u2010iodosuccinimide)\u2010mediated cycloisomerization reactions of 1\u2010(2\u2032\u2010anilinyl)prop\u20102\u2010yn\u20101\u2010ols to <jats:italic>gem<\/jats:italic>\u20103\u2010(diiodomethyl)indolin\u20102\u2010ones and 2\u2010(iodomethylene)indolin\u20103\u2010ones has been developed. The reactions were shown to be chemoselective, with secondary and tertiary alcoholic substrates exclusively giving the 3\u2010 and 2\u2010oxindole products, respectively. In the case of the latter, the transformation features an unprecedented double 1,2\u2010OH and 1,2\u2010alkyl migration relay. Density functional theory (DFT) calculations based on proposed iodoaminocyclization species provide insight into this unique divergence in product selectivity.<\/jats:p>","DOI":"10.1002\/chem.201202606","type":"journal-article","created":{"date-parts":[[2012,11,30]],"date-time":"2012-11-30T14:37:19Z","timestamp":1354286239000},"page":"1978-1985","source":"Crossref","is-referenced-by-count":21,"title":["1\u2010(2\u2032\u2010Anilinyl)prop\u20102\u2010yn\u20101\u2010ol Rearrangement for Oxindole Synthesis"],"prefix":"10.1002","volume":"19","author":[{"given":"Prasath","family":"Kothandaraman","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Bing Qin","family":"Koh","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Taweetham","family":"Limpanuparb","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hajime","family":"Hirao","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Philip Wai Hong","family":"Chan","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2012,11,30]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"Selected recent reviews:"},{"key":"e_1_2_6_2_2","first-page":"213","volume":"3","author":"Gawad N. M. A.","year":"2011","journal-title":"Int. J. Pharm. Pharm. Sci."},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1039\/C1SC00544H"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201100836"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201000161"},{"key":"e_1_2_6_6_2","first-page":"758","volume":"13","author":"Badillo J. J.","year":"2010","journal-title":"Curr. Opin. Drug Discovery Dev."},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0029-1216975"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200701342"},{"key":"e_1_2_6_8_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200701342"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)99384-6"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)97170-9"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4020(72)80014-0"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/np990408d"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm00127a014"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/np800471y"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200604377"},{"key":"e_1_2_6_15_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200604377"},{"key":"e_1_2_6_16_2","unstructured":"Selected recent examples:"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol202263a"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol2005243"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol1027305"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200904393"},{"key":"e_1_2_6_20_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200904393"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol801168j"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200502252"},{"key":"e_1_2_6_22_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200502252"},{"key":"e_1_2_6_23_2","unstructured":"Selected recent reviews:"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201100324"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr100214d"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1039\/b909978f"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2006-950405"},{"key":"e_1_2_6_28_2","unstructured":"Selected recent examples:"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201102453"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo902603v"},{"key":"e_1_2_6_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja805326f"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2008.07.061"},{"key":"e_1_2_6_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200701392"},{"key":"e_1_2_6_33_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200701392"},{"key":"e_1_2_6_34_2","unstructured":"\u00a0"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol2007154"},{"key":"e_1_2_6_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol103074d"},{"key":"e_1_2_6_37_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2011.08.084"},{"key":"e_1_2_6_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/cc100015k"},{"key":"e_1_2_6_39_2","first-page":"1243","author":"Choi J.","year":"2008","journal-title":"Synlett"},{"key":"e_1_2_6_40_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2007.08.097"},{"key":"e_1_2_6_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol052518j"},{"key":"e_1_2_6_42_2","unstructured":"For reviews on alcohol proelectrophiles see:"},{"key":"e_1_2_6_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201100858"},{"key":"e_1_2_6_44_2","doi-asserted-by":"publisher","DOI":"10.1039\/b823217b"},{"key":"e_1_2_6_45_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200804114"},{"key":"e_1_2_6_45_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200804114"},{"key":"e_1_2_6_46_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2008.04.018"},{"key":"e_1_2_6_47_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200601050"},{"key":"e_1_2_6_48_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2005.02.026"},{"key":"e_1_2_6_49_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200500076"},{"key":"e_1_2_6_50_2","unstructured":"\u00a0"},{"key":"e_1_2_6_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo301198z"},{"key":"e_1_2_6_52_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201200578"},{"key":"e_1_2_6_53_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201101363"},{"key":"e_1_2_6_54_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo201208e"},{"key":"e_1_2_6_55_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo102374z"},{"key":"e_1_2_6_56_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201000341"},{"key":"e_1_2_6_56_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201000341"},{"key":"e_1_2_6_57_2","unstructured":"For 1 2\u2010OH migrations see:"},{"key":"e_1_2_6_58_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00214-009-0657-2"},{"key":"e_1_2_6_59_2","doi-asserted-by":"publisher","DOI":"10.1021\/bi7018095"},{"key":"e_1_2_6_60_2","doi-asserted-by":"publisher","DOI":"10.1007\/BF00906657"},{"key":"e_1_2_6_61_2","unstructured":"For double migrations see:"},{"key":"e_1_2_6_62_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja301243t"},{"key":"e_1_2_6_63_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201103472"},{"key":"e_1_2_6_64_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200900391"},{"key":"e_1_2_6_65_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja803579z"},{"key":"e_1_2_6_66_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200501517"},{"key":"e_1_2_6_67_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja017323v"},{"key":"e_1_2_6_68_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19740862409"},{"key":"e_1_2_6_68_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.197408131"},{"key":"e_1_2_6_69_2","unstructured":"Please see the Supporting Information for details."},{"key":"e_1_2_6_70_2","unstructured":"CCDC\u2010884060 (2\u2009a) and CCDC\u2010884061 (3\u2009a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre viawww.ccdc.cam.ac.uk\/data_request\/cif."},{"key":"e_1_2_6_71_2","unstructured":"Gaussian\u200509 Revision\u2005B.01 M.\u2005J. Frisch G.\u2005W. Trucks H.\u2005B. Schlegel G.\u2005E. Scuseria M.\u2005A. Robb J.\u2005R. Cheeseman G. Scalmani V. Barone B. Mennucci G.\u2005A. Petersson H. Nakatsuji M. Caricato X. Li H.\u2005P. Hratchian A.\u2005F. Izmaylov J. Bloino G. Zheng J.\u2005L. Sonnenberg M. Hada M. Ehara K. Toyota R. Fukuda J. Hasegawa M. Ishida T. Nakajima Y. Honda O. Kitao H. Nakai T. Vreven J.\u2005A. Montgomery Jr. J.\u2005E. Peralta F. Ogliaro M. Bearpark J.\u2005J. Heyd E. Brothers K.\u2005N. Kudin V.\u2005N. Staroverov R. Kobayashi J. Normand K. Raghavachari A. Rendell J.\u2005C. Burant S.\u2005S. Iyengar J. Tomasi M. Cossi N. Rega J.\u2005M. Millam M. Klene J.\u2005E. Knox J.\u2005B. Cross V. Bakken C. Adamo J. Jaramillo R. Gomperts R.\u2005E. Stratmann O. Yazyev A.\u2005J. Austin R. Cammi C. Pomelli J.\u2005W. Ochterski R.\u2005L. Martin K. Morokuma V.\u2005G. Zakrzewski G.\u2005A. Voth P. Salvador J.\u2005J. Dannenberg S. Dapprich A.\u2005D. Daniels \u00d6. Farkas J.\u2005B. Foresman J.\u2005V. Ortiz J. Cioslowski D.\u2005J. Fox Gaussian Inc. Wallingford CT 2009."},{"key":"e_1_2_6_72_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.464913"},{"key":"e_1_2_6_73_2","doi-asserted-by":"publisher","DOI":"10.1103\/PhysRevB.37.785"},{"key":"e_1_2_6_74_2","doi-asserted-by":"publisher","DOI":"10.1139\/p80-159"},{"key":"e_1_2_6_75_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.452288"},{"key":"e_1_2_6_76_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00267a063"},{"key":"e_1_2_6_77_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.474659"},{"key":"e_1_2_6_78_2","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.20084"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.201202606","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201202606","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T19:05:37Z","timestamp":1760295937000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.201202606"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2012,11,30]]},"references-count":86,"journal-issue":{"issue":"6","published-print":{"date-parts":[[2013,2,4]]}},"alternative-id":["10.1002\/chem.201202606"],"URL":"https:\/\/doi.org\/10.1002\/chem.201202606","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"type":"print","value":"0947-6539"},{"type":"electronic","value":"1521-3765"}],"subject":[],"published":{"date-parts":[[2012,11,30]]}}}