{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,4]],"date-time":"2026-10-04T17:51:29Z","timestamp":1791136289824,"version":"4.1.0"},"reference-count":64,"publisher":"Wiley","issue":"25","license":[{"start":{"date-parts":[[2012,5,8]],"date-time":"2012-05-08T00:00:00Z","timestamp":1336435200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2012,6,18]]},"DOI":"10.1002\/anie.201201505","type":"journal-article","created":{"date-parts":[[2012,5,8]],"date-time":"2012-05-08T09:53:03Z","timestamp":1336470783000},"page":"6214-6218","source":"Crossref","is-referenced-by-count":26,"title":["Chromium(0)\u2010Catalyzed Tandem Cyclization of \u03b1,\u03b2\u2010Unsaturated Thioimidates Containing an Enyne Moiety"],"prefix":"10.1002","volume":"51","author":[{"given":"Yusuke","family":"Karibe","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hiroyuki","family":"Kusama","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nobuharu","family":"Iwasawa","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2012,5,8]]},"reference":[{"key":"e_1_2_3_1_2","unstructured":"For recent reviews of 1\u2010azabicyclo[n.3.0] ring systems see:"},{"key":"e_1_2_3_2_2","doi-asserted-by":"publisher","DOI":"10.1039\/b108975g"},{"key":"e_1_2_3_3_2","doi-asserted-by":"publisher","DOI":"10.1039\/b509525p"},{"key":"e_1_2_3_4_2","first-page":"617","volume-title":"The Way of Synthesis","author":"Hudlicky T.","year":"2007"},{"key":"e_1_2_3_5_2","unstructured":"For recent reviews of stemona alkaloids see:"},{"key":"e_1_2_3_6_2","doi-asserted-by":"publisher","DOI":"10.1039\/c005018k"},{"key":"e_1_2_3_7_2","doi-asserted-by":"publisher","DOI":"10.1039\/a902437i"},{"key":"e_1_2_3_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200900037"},{"key":"e_1_2_3_9_2","unstructured":"\u00a0"},{"key":"e_1_2_3_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol702563p"},{"key":"e_1_2_3_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja055629m"},{"key":"e_1_2_3_12_2","unstructured":"Thioimidates were chosen as substrates because of their higher stability compared to imidates and higher nucleophilicity compared to imines."},{"key":"e_1_2_3_13_2","unstructured":"For recent reviews on electrophilic activation of alkynes see:"},{"key":"e_1_2_3_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200604335"},{"key":"e_1_2_3_14_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200604335"},{"key":"e_1_2_3_15_2","doi-asserted-by":"publisher","DOI":"10.1039\/B612008C"},{"key":"e_1_2_3_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200601522"},{"key":"e_1_2_3_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr078361l"},{"key":"e_1_2_3_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr050041j"},{"key":"e_1_2_3_19_2","doi-asserted-by":"publisher","DOI":"10.1039\/b816696j"},{"key":"e_1_2_3_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr068434l"},{"key":"e_1_2_3_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr068435d"},{"key":"e_1_2_3_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr068430g"},{"key":"e_1_2_3_23_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2008.04.018"},{"key":"e_1_2_3_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr000436x"},{"key":"e_1_2_3_25_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature05592"},{"key":"e_1_2_3_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200602454"},{"key":"e_1_2_3_26_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200602454"},{"key":"e_1_2_3_27_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200600399"},{"key":"e_1_2_3_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo070579k"},{"key":"e_1_2_3_29_2","doi-asserted-by":"publisher","DOI":"10.1039\/b807499m"},{"key":"e_1_2_3_30_2","unstructured":"The reactions of1\u2009a\u20131\u2009j 1\u2009m 1\u2009nwere examined using a mixture ofZandE\u2005isomers concerning the thioimidate moiety. It was confirmed that isomerization of the zwitterionic intermediates occurred easily and there seemed to be no difference in reactivity betweenZandE\u2005isomer. See the Supporting Information (8)."},{"key":"e_1_2_3_31_2","unstructured":"For recent reviews on gold\u2010mediated homogeneous catalysis see:"},{"key":"e_1_2_3_32_2","doi-asserted-by":"publisher","DOI":"10.3762\/bjoc.7.103"},{"key":"e_1_2_3_33_2","doi-asserted-by":"publisher","DOI":"10.3762\/bjoc.7.124"},{"key":"e_1_2_3_34_2","unstructured":"When the reaction of thioimidate1\u2009awas carried out with [Cr(CO)6] (10 mol\u2009%) in the presence of2\u2009aor 1 4\u2010diphenyl\u20102\u2010methylthio\u20101\u2010azabuta\u20101 3\u2010diene the rate of conversion of1\u2009abecame lower. Furthermore in the reaction of2\u2009awith [Cr(CO)6] under photoirradiation the complex that was formed by the coordination of chromium to the sulfur atom was observed. For details see the Supporting Information (7.1 7.2)."},{"key":"e_1_2_3_35_2","unstructured":"We reported one example of a similar reaction of imines where the reaction proceeded without the thio substituent owing to the facile ring closure of the rigidity of the aromatic substrate see:"},{"key":"e_1_2_3_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0529795"},{"key":"e_1_2_3_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja027589h"},{"key":"e_1_2_3_38_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.2004.16"},{"key":"e_1_2_3_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol052610f"},{"key":"e_1_2_3_40_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2011.04.017"},{"key":"e_1_2_3_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo050711l"},{"key":"e_1_2_3_42_2","unstructured":"\u00a0"},{"key":"e_1_2_3_43_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0671924"},{"key":"e_1_2_3_44_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201001003"},{"key":"e_1_2_3_45_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200461559"},{"key":"e_1_2_3_45_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200461559"},{"key":"e_1_2_3_46_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0782605"},{"key":"e_1_2_3_47_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201001061"},{"key":"e_1_2_3_47_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201001061"},{"key":"e_1_2_3_48_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201003019"},{"key":"e_1_2_3_49_2","unstructured":"The structure and relative stereochemistry of2\u2009pwere confirmed by X\u2010ray analysis after hydrolysis of theN S\u2010keteneacetal moiety. See the Supporting Information (6.1)."},{"key":"e_1_2_3_50_2","unstructured":"Photoirradiation is important for facile generation of the catalytically active coordinatively unsaturated species from [Cr(CO)6] at ambient temperature. See the Supporting Information (7.3)."},{"key":"e_1_2_3_51_2","unstructured":"For reviews of 1 7\u2010electrocyclization see:"},{"key":"e_1_2_3_52_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2008-1072743"},{"key":"e_1_2_3_53_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200500892"},{"key":"e_1_2_3_54_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1991-26413"},{"key":"e_1_2_3_55_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja803890t"},{"key":"e_1_2_3_56_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.19960020116"},{"key":"e_1_2_3_57_2","unstructured":"In the reaction of \u03c9\u2010acetylenic thioimidate7with [W(CO)6] (3\u2005equiv) in toluene under photoirradiation the zwitterionic complex8was obtained.We have succeeded in obtaining a single crystal that was suitable for X\u2010ray analysis for the CF3\u2010substituted complex by recrystallization from pentane\/CH2Cl2in a nitrogen atmosphere. For details see the Supporting Information (8).Crystal data: monoclinic P21\/n a=11.4793(4) b=16.9217(6) c=11.5189(4)\u2005\u00c5 \u03b1=90.00 \u03b2=106.2280(10) \u03b3=90.00\u00b0 R\u2010factor=3.37 (%)."},{"key":"e_1_2_3_58_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00073a017"},{"key":"e_1_2_3_58_3","doi-asserted-by":"publisher","DOI":"10.1021\/ja108586d"},{"key":"e_1_2_3_59_2","unstructured":"The relative configuration of5\u2005nwas determined by observation of NOE spectra. For details see the Supporting Information (6.3)."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201201505","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201201505","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,16]],"date-time":"2023-10-16T12:31:42Z","timestamp":1697459502000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201201505"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2012,5,8]]},"references-count":64,"journal-issue":{"issue":"25","published-print":{"date-parts":[[2012,6,18]]}},"alternative-id":["10.1002\/anie.201201505"],"URL":"https:\/\/doi.org\/10.1002\/anie.201201505","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2012,5,8]]}}}