{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,13]],"date-time":"2026-10-13T02:56:20Z","timestamp":1791860180698,"version":"4.3.4"},"reference-count":48,"publisher":"Wiley","issue":"32","license":[{"start":{"date-parts":[[2019,6,4]],"date-time":"2019-06-04T00:00:00Z","timestamp":1559606400000},"content-version":"am","delay-in-days":330,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#am"},{"start":{"date-parts":[[2018,7,9]],"date-time":"2018-07-09T00:00:00Z","timestamp":1531094400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/100000165","name":"Division of Chemistry","doi-asserted-by":"publisher","award":["CHE-1464690"],"award-info":[{"award-number":["CHE-1464690"]}],"id":[{"id":"10.13039\/100000165","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000165","name":"Division of Chemistry","doi-asserted-by":"publisher","award":["1625963"],"award-info":[{"award-number":["1625963"]}],"id":[{"id":"10.13039\/100000165","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000057","name":"National Institute of General Medical Sciences","doi-asserted-by":"publisher","award":["GM07717"],"award-info":[{"award-number":["GM07717"]}],"id":[{"id":"10.13039\/100000057","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":[[2018,8,6]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Enoldiazoimides, a new subclass of enoldiazo compounds, generate enol\u2010substituted carbonyl ylides whose reactions with sulfur ylides enable an unprecedented formal [4+2]\u2005cycloaddition. The resulting multifunctionalized indolizidinones, which incorporate sulfur, are formed in good yields under mild reaction conditions. The uniqueness of this transformation stems from the role of the silyl\u2010protected enol, since the corresponding acetyldiazoimide failed to provide any cross\u2010products in metal\u2010catalyzed reactions with sulfur ylides. This copper\u2010catalyzed cycloaddition is initiated with the generation of enol\u2010substituted carbonyl ylides and sulfur ylides from enoldiazoimides and sulfonium salts, respectively, and proceeds through stepwise six\u2010membered ring formation, C\u2212O and C\u2212S bond cleavage, and silyl and acetyl group migration.<\/jats:p>","DOI":"10.1002\/anie.201805323","type":"journal-article","created":{"date-parts":[[2018,6,4]],"date-time":"2018-06-04T12:21:40Z","timestamp":1528114900000},"page":"10343-10346","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":26,"title":["Copper\u2010Catalyzed Formal [4+2] Cycloaddition of Enoldiazoimides with Sulfur Ylides"],"prefix":"10.1002","volume":"57","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-6554-1789","authenticated-orcid":false,"given":"Qing\u2010Qing","family":"Cheng","sequence":"first","affiliation":[{"name":"Department of Chemistry The University of Texas at San Antonio  One UTSA Circle San Antonio TX 78249 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lyn\u00e9e A.","family":"Massey","sequence":"additional","affiliation":[{"name":"Department of Chemistry The University of Texas at San Antonio  One UTSA Circle San Antonio TX 78249 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Brook S.","family":"Willett","sequence":"additional","affiliation":[{"name":"Department of Chemistry The University of Texas at San Antonio  One UTSA Circle San Antonio TX 78249 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yongming","family":"Deng","sequence":"additional","affiliation":[{"name":"Department of Chemistry The University of Texas at San Antonio  One UTSA Circle San Antonio TX 78249 USA"},{"name":"Current address: Department of Chemistry Western Kentucky University  Bowling Green KY 42101 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hadi","family":"Arman","sequence":"additional","affiliation":[{"name":"Department of Chemistry The University of Texas at San Antonio  One UTSA Circle San Antonio TX 78249 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1386-3780","authenticated-orcid":false,"given":"Michael P.","family":"Doyle","sequence":"additional","affiliation":[{"name":"Department of Chemistry The University of Texas at San Antonio  One UTSA Circle San Antonio TX 78249 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2018,7,9]]},"reference":[{"key":"e_1_2_2_1_1","unstructured":"For reviews see:"},{"key":"e_1_2_2_2_2","volume-title":"Nitrogen, Oxygen and Sulfur Ylide Chemistry: A Practical Approach in Chemistry","year":"2002"},{"key":"e_1_2_2_3_2","volume-title":"Modern Ylide Chemistry: Applications in Ligand Design, Organic and Catalytic Transformations","year":"2018"},{"key":"e_1_2_2_4_1","unstructured":"For reviews see:"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/b000708k"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.200590109"},{"key":"e_1_2_2_7_2","first-page":"133","volume":"80","author":"Hodgson D. 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React."},{"key":"e_1_2_2_8_1","unstructured":"For reviews see:"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr950022h"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1039\/b816701j"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2011.07.009"},{"key":"e_1_2_2_12_1","unstructured":"For reviews see:"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr960411r"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr068402y"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6CS00276E"},{"key":"e_1_2_2_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201704069"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201704069"},{"key":"e_1_2_2_17_1","unstructured":"Both rhodium and copper catalysts were tested in reactions of either \u03b1-diazoimides1\u2009aor2\u2009awith the sulfur ylide3\u2009a."},{"key":"e_1_2_2_18_1","unstructured":"For reviews see:"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7CS00324B"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/cctc.201701346"},{"key":"e_1_2_2_21_1","unstructured":"For selected examples see:"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja207664r"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b10860"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201601260"},{"key":"e_1_2_2_24_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201601260"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b05840"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201706639"},{"key":"e_1_2_2_26_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201706639"},{"key":"e_1_2_2_27_1","unstructured":"For experimental details see Section\u20052 of the Supporting Information."},{"key":"e_1_2_2_28_1","unstructured":"For reviews see:"},{"key":"e_1_2_2_29_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0140-6736(03)13780-4"},{"key":"e_1_2_2_30_2","doi-asserted-by":"publisher","DOI":"10.1038\/nrc1977"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0780210"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr900097c"},{"key":"e_1_2_2_33_2","doi-asserted-by":"publisher","DOI":"10.1038\/nrd3404"},{"key":"e_1_2_2_34_1","unstructured":"Only a trace amount of5\u2009awas formed after4\u2009awas fully consumed."},{"key":"e_1_2_2_35_1","unstructured":"CCDC\u20051821831(5\u2009d) contains the supplementary crystallographic data for this paper. 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