{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,7]],"date-time":"2026-10-07T19:45:18Z","timestamp":1791402318708,"version":"4.3.3"},"reference-count":86,"publisher":"Wiley","issue":"24","license":[{"start":{"date-parts":[[2018,5,14]],"date-time":"2018-05-14T00:00:00Z","timestamp":1526256000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001711","name":"Schweizerischer Nationalfonds zur F\u00f6rderung der Wissenschaftlichen Forschung","doi-asserted-by":"publisher","award":["20_172497"],"award-info":[{"award-number":["20_172497"]}],"id":[{"id":"10.13039\/501100001711","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100006389","name":"Universit\u00e9 de Gen\u00e8ve","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100006389","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2018,6,11]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Polycyclic indoline\u2010benzodiazepines can be accessed through the intermolecular reaction of Tr\u00f6ger bases with <jats:italic>N<\/jats:italic>\u2010sulfonyl\u20101,2,3\u2010triazoles. Under Rh<jats:sup>II<\/jats:sup> catalysis, \u03b1\u2010imino carbenes are generated and a subsequent cascade of [1,2]\u2010Stevens, Friedel\u2013Crafts, Grob, and aminal formation reactions yield the polycyclic heterocycles as single isomers (d.r.&gt;49:1, four stereocenters including two bridgehead N\u2005atoms). Further ring expansion by insertion of a second \u03b1\u2010imino carbene leads to elaborated polycyclic 9\u2010membered\u2010ring triazonanes.<\/jats:p>","DOI":"10.1002\/anie.201803756","type":"journal-article","created":{"date-parts":[[2018,4,19]],"date-time":"2018-04-19T19:20:10Z","timestamp":1524165610000},"page":"7151-7155","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":59,"title":["Polycyclic Indoline\u2010Benzodiazepines through Electrophilic Additions of \u03b1\u2010Imino Carbenes to Tr\u00f6ger Bases"],"prefix":"10.1002","volume":"57","author":[{"given":"Alessandro","family":"Bosmani","sequence":"first","affiliation":[{"name":"D\u00e9partement de Chimie Organique Universit\u00e9 de Gen\u00e8ve  quai Ernest Ansermet 30 1211 Geneva 4 Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alejandro","family":"Guarnieri\u2010Ib\u00e1\u00f1ez","sequence":"additional","affiliation":[{"name":"D\u00e9partement de Chimie Organique Universit\u00e9 de Gen\u00e8ve  quai Ernest Ansermet 30 1211 Geneva 4 Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"S\u00e9bastien","family":"Goudedranche","sequence":"additional","affiliation":[{"name":"D\u00e9partement de Chimie Organique Universit\u00e9 de Gen\u00e8ve  quai Ernest Ansermet 30 1211 Geneva 4 Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"C\u00e9line","family":"Besnard","sequence":"additional","affiliation":[{"name":"Laboratoire de Cristallographie Universit\u00e9 de Gen\u00e8ve  quai Ernest Ansermet 24 1211 Geneva 4 Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6247-8059","authenticated-orcid":false,"given":"J\u00e9r\u00f4me","family":"Lacour","sequence":"additional","affiliation":[{"name":"D\u00e9partement de Chimie Organique Universit\u00e9 de Gen\u00e8ve  quai Ernest Ansermet 30 1211 Geneva 4 Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2018,5,14]]},"reference":[{"key":"e_1_2_2_1_1","unstructured":"\u00a0"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5"},{"key":"e_1_2_2_2_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20010601)113:11<2056::AID-ANGE2056>3.0.CO;2-W"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20020315)41:6<1053::AID-ANIE1053>3.0.CO;2-4"},{"key":"e_1_2_2_3_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20020315)114:6<1095::AID-ANGE1095>3.0.CO;2-3"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr9001462"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/B901975H"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr200409f"},{"key":"e_1_2_2_7_1","unstructured":"\u00a0"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00835a057"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1039\/c29710000296"},{"key":"e_1_2_2_10_1","unstructured":"\u00a0"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201104807"},{"key":"e_1_2_2_11_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201104807"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201209338"},{"key":"e_1_2_2_12_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201209338"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4CS00072B"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0034-1379303"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0034-1380444"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201601703"},{"key":"e_1_2_2_17_1","unstructured":"\u00a0"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200700804"},{"key":"e_1_2_2_18_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200700804"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja908075u"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja202969z"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol201949h"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201302653"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja401380d"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201405357"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja5096045"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol5012532"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201504013"},{"key":"e_1_2_2_27_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201504013"},{"key":"e_1_2_2_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b04295"},{"key":"e_1_2_2_29_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201501260"},{"key":"e_1_2_2_29_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201501260"},{"key":"e_1_2_2_30_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0034-1379636"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6b01298"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7SC00964J"},{"key":"e_1_2_2_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201612585"},{"key":"e_1_2_2_33_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201612585"},{"key":"e_1_2_2_34_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201709384"},{"key":"e_1_2_2_34_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201709384"},{"key":"e_1_2_2_35_1","doi-asserted-by":"publisher","DOI":"10.1039\/b604828p"},{"key":"e_1_2_2_36_1","unstructured":"\u00a0"},{"key":"e_1_2_2_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja400350c"},{"key":"e_1_2_2_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo501785d"},{"key":"e_1_2_2_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja5061609"},{"key":"e_1_2_2_40_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201506764"},{"key":"e_1_2_2_40_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201506764"},{"key":"e_1_2_2_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5b02570"},{"key":"e_1_2_2_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol503247t"},{"key":"e_1_2_2_43_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.5b00036"},{"key":"e_1_2_2_44_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201406460"},{"key":"e_1_2_2_45_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5CC00268K"},{"key":"e_1_2_2_46_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.6b02389"},{"key":"e_1_2_2_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b00180"},{"key":"e_1_2_2_48_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6SC01075J"},{"key":"e_1_2_2_49_1","unstructured":"\u00a0"},{"key":"e_1_2_2_50_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr940066a"},{"key":"e_1_2_2_51_2","doi-asserted-by":"publisher","DOI":"10.2174\/1385272819666150714182732"},{"key":"e_1_2_2_52_1","unstructured":"In relation to compounds3and4 vinblastine is an interesting example since it contains not only the indoline skeleton but also a 9-membered ring in the second fragment."},{"key":"e_1_2_2_53_1","unstructured":"\u00a0"},{"key":"e_1_2_2_54_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr60256a004"},{"key":"e_1_2_2_55_2","doi-asserted-by":"publisher","DOI":"10.1039\/c005345g"},{"key":"e_1_2_2_56_1","unstructured":"\u00a0"},{"key":"e_1_2_2_57_2","doi-asserted-by":"publisher","DOI":"10.1002\/prac.18870360123"},{"key":"e_1_2_2_58_2","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.194402701143"},{"key":"e_1_2_2_59_2","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.200800329"},{"key":"e_1_2_2_60_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201201249"},{"key":"e_1_2_2_61_1","unstructured":"The aminal opening is induced by the N-atom quaternization. See the following references and discussion therein:"},{"key":"e_1_2_2_62_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201100134"},{"key":"e_1_2_2_62_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201100134"},{"key":"e_1_2_2_63_2","doi-asserted-by":"publisher","DOI":"10.1039\/C1OB06751F"},{"key":"e_1_2_2_64_1","unstructured":"A third stereochemical representation of compounds3is provided in Scheme\u20053."},{"key":"e_1_2_2_65_1","unstructured":"In TB and derivatives the bridgehead nitrogen atoms are stereogenic and configurationally stable under neutral conditions."},{"key":"e_1_2_2_66_1","unstructured":"With TB-carrying substituentsorthoto the nitrogen atoms only traces of the desired products were observed with very small conversion of starting materials."},{"key":"e_1_2_2_67_1","unstructured":"With twop-nitro substituents only traces of conversion are observed."},{"key":"e_1_2_2_68_1","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(95)01316-A"},{"key":"e_1_2_2_69_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol3029127"},{"key":"e_1_2_2_70_1","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.19550380306"},{"key":"e_1_2_2_71_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201700845"},{"key":"e_1_2_2_72_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja4111418"},{"key":"e_1_2_2_73_1","unstructured":"Compound4Owas first identified in the crude mixture of the reaction of1Owith2\u2009aas a byproduct."},{"key":"e_1_2_2_74_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo101727r"},{"key":"e_1_2_2_75_1","unstructured":"CCDC\u20051832809\u2005(4\u2009O) 1832810\u2005(3\u2009aA) and 1832811\u2005(3\u2009lA) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge fromThe Cambridge Crystallographic Data Centre."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201803756","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201803756","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,9,18]],"date-time":"2023-09-18T13:54:27Z","timestamp":1695045267000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201803756"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,5,14]]},"references-count":86,"journal-issue":{"issue":"24","published-print":{"date-parts":[[2018,6,11]]}},"alternative-id":["10.1002\/anie.201803756"],"URL":"https:\/\/doi.org\/10.1002\/anie.201803756","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,5,14]]},"assertion":[{"value":"2018-03-28","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2018-05-14","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}