{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,9]],"date-time":"2026-05-09T14:53:15Z","timestamp":1778338395627,"version":"3.51.4"},"reference-count":110,"publisher":"Wiley","issue":"25","license":[{"start":{"date-parts":[[2019,5,10]],"date-time":"2019-05-10T00:00:00Z","timestamp":1557446400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/100000002","name":"National Institutes of Health","doi-asserted-by":"publisher","award":["S10 OD021758-01A1"],"award-info":[{"award-number":["S10 OD021758-01A1"]}],"id":[{"id":"10.13039\/100000002","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":[[2019,6,17]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The first catalytic enantioselective alkynylation of chromones is reported. In this process, chromones are silylated to form silyloxybenzopyrylium ions that lead to silyl enol ethers after Cu\u2010catalyzed alkyne addition using StackPhos as a ligand. The outcome of the reaction is impacted by distal ligand substituents with differing electronic character and it was found that successful reactions could be achieved with different ligand congeners by using different solvents. This sequence enables access to different products by protonation or further functionalization, thus increasing complexity in a divergent manner. The transformation is high yielding over a broad scope to provide a variety of useful chromanones in high enantioselectivity.<\/jats:p>","DOI":"10.1002\/anie.201902405","type":"journal-article","created":{"date-parts":[[2019,4,24]],"date-time":"2019-04-24T02:12:03Z","timestamp":1556071923000},"page":"8416-8420","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":51,"title":["A Facile Enantioselective Alkynylation of Chromones"],"prefix":"10.1002","volume":"58","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-0412-8111","authenticated-orcid":false,"given":"Lindsey G.","family":"DeRatt","sequence":"first","affiliation":[{"name":"Florida Center for Heterocyclic Compounds &amp; Department of Chemistry University of Florida  P.O. Box 117200 Gainesville FL 32607 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1515-9455","authenticated-orcid":false,"given":"Mukesh","family":"Pappoppula","sequence":"additional","affiliation":[{"name":"Florida Center for Heterocyclic Compounds &amp; Department of Chemistry University of Florida  P.O. Box 117200 Gainesville FL 32607 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4576-638X","authenticated-orcid":false,"given":"Aaron","family":"Aponick","sequence":"additional","affiliation":[{"name":"Florida Center for Heterocyclic Compounds &amp; Department of Chemistry University of Florida  P.O. Box 117200 Gainesville FL 32607 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2019,5,10]]},"reference":[{"key":"e_1_2_2_1_1","unstructured":"\u00a0"},{"key":"e_1_2_2_2_2","volume-title":"Comprehensive Asymmetric Catalysis","year":"1999"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0401811101"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.3762\/bjoc.13.8"},{"key":"e_1_2_2_5_1","unstructured":"\u00a0"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0307152101"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20010105)40:1<92::AID-ANIE92>3.0.CO;2-K"},{"key":"e_1_2_2_7_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20010105)113:1<96::AID-ANGE96>3.0.CO;2-B"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr020025b"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2005.03.022"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.7b03759"},{"key":"e_1_2_2_11_1","unstructured":"\u00a0"},{"key":"e_1_2_2_12_2","volume-title":"Privileged Chiral Ligands and Catalysts","year":"2011"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1083622"},{"key":"e_1_2_2_14_1","unstructured":"For reviews see:"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201205449"},{"key":"e_1_2_2_15_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201205449"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201205343"},{"key":"e_1_2_2_16_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201205343"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.1405"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr5001496"},{"key":"e_1_2_2_19_2","volume-title":"Acid Catalysis in Modern Organic Synthesis","year":"2008"},{"key":"e_1_2_2_20_2","first-page":"77","volume":"40","author":"Ooi T.","year":"2007","journal-title":"Aldrichimica Acta"},{"key":"e_1_2_2_21_1","unstructured":"\u00a0"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b04686"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja801514m"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b05225"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b00260"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1176758"},{"key":"e_1_2_2_27_1","unstructured":"\u00a0"},{"key":"e_1_2_2_28_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201806312"},{"key":"e_1_2_2_28_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201806312"},{"key":"e_1_2_2_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b11993"},{"key":"e_1_2_2_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b05939"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja206997e"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.6b01384"},{"key":"e_1_2_2_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b12832"},{"key":"e_1_2_2_34_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6b01783"},{"key":"e_1_2_2_35_1","unstructured":"\u00a0"},{"key":"e_1_2_2_36_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201307371"},{"key":"e_1_2_2_36_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201307371"},{"key":"e_1_2_2_37_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201100346"},{"key":"e_1_2_2_38_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200705344"},{"key":"e_1_2_2_38_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200705344"},{"key":"e_1_2_2_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja053386s"},{"key":"e_1_2_2_40_1","unstructured":"\u00a0"},{"key":"e_1_2_2_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja207585p"},{"key":"e_1_2_2_42_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201507373"},{"key":"e_1_2_2_42_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201507373"},{"key":"e_1_2_2_43_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.5b00364"},{"key":"e_1_2_2_44_1","unstructured":"\u00a0"},{"key":"e_1_2_2_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja407689a"},{"key":"e_1_2_2_46_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201507848"},{"key":"e_1_2_2_46_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201507848"},{"key":"e_1_2_2_47_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201507849"},{"key":"e_1_2_2_47_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201507849"},{"key":"e_1_2_2_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b13387"},{"key":"e_1_2_2_49_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.7b00133"},{"key":"e_1_2_2_50_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b00363"},{"key":"e_1_2_2_51_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(02)02857-5"},{"key":"e_1_2_2_52_1","unstructured":"\u00a0"},{"key":"e_1_2_2_53_2","doi-asserted-by":"publisher","DOI":"10.1002\/9780470187012"},{"key":"e_1_2_2_54_2","doi-asserted-by":"publisher","DOI":"10.1039\/np9860300465"},{"key":"e_1_2_2_55_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200800035"},{"key":"e_1_2_2_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/np100730b"},{"key":"e_1_2_2_57_2","doi-asserted-by":"publisher","DOI":"10.1080\/10575639608043238"},{"key":"e_1_2_2_58_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b08695"},{"key":"e_1_2_2_59_1","unstructured":"\u00a0"},{"key":"e_1_2_2_60_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201101228"},{"key":"e_1_2_2_61_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja070394v"},{"key":"e_1_2_2_62_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201302573"},{"key":"e_1_2_2_62_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201302573"},{"key":"e_1_2_2_63_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol2004148"},{"key":"e_1_2_2_64_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201203643"},{"key":"e_1_2_2_65_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39860001592"},{"key":"e_1_2_2_66_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja1005477"},{"key":"e_1_2_2_67_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200803326"},{"key":"e_1_2_2_67_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200803326"},{"key":"e_1_2_2_68_1","unstructured":"\u00a0"},{"key":"e_1_2_2_69_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200501251"},{"key":"e_1_2_2_69_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200501251"},{"key":"e_1_2_2_70_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3cc43105c"},{"key":"e_1_2_2_71_1","unstructured":"\u00a0"},{"key":"e_1_2_2_72_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200390319"},{"key":"e_1_2_2_72_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200390290"},{"key":"e_1_2_2_73_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201007560"},{"key":"e_1_2_2_73_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201007560"},{"key":"e_1_2_2_74_1","unstructured":"\u00a0"},{"key":"e_1_2_2_75_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201600547"},{"key":"e_1_2_2_75_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201600547"},{"key":"e_1_2_2_76_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.8b00377"},{"key":"e_1_2_2_77_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr9603744"},{"key":"e_1_2_2_78_1","unstructured":"\u00a0"},{"key":"e_1_2_2_79_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr60307a002"},{"key":"e_1_2_2_80_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.2741"},{"key":"e_1_2_2_81_2","doi-asserted-by":"publisher","DOI":"10.1039\/b922984a"},{"key":"e_1_2_2_82_1","unstructured":"\u00a0"},{"key":"e_1_2_2_83_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja963275g"},{"key":"e_1_2_2_84_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol4028732"},{"key":"e_1_2_2_85_1","unstructured":"\u00a0"},{"key":"e_1_2_2_86_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr980381n"},{"key":"e_1_2_2_87_2","doi-asserted-by":"publisher","DOI":"10.1038\/ncomms10109"},{"key":"e_1_2_2_88_1","doi-asserted-by":"publisher","DOI":"10.1071\/CH9762023"},{"key":"e_1_2_2_89_1","unstructured":"\u00a0"},{"key":"e_1_2_2_90_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201003469"},{"key":"e_1_2_2_90_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201003469"},{"key":"e_1_2_2_91_2","doi-asserted-by":"publisher","DOI":"10.3987\/COM-05-10652"},{"key":"e_1_2_2_92_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00088a015"},{"key":"e_1_2_2_93_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol901901m"},{"key":"e_1_2_2_94_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol302273r"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201902405","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201902405","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.201902405","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201902405","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,9,9]],"date-time":"2023-09-09T15:40:48Z","timestamp":1694274048000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201902405"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,5,10]]},"references-count":110,"journal-issue":{"issue":"25","published-print":{"date-parts":[[2019,6,17]]}},"alternative-id":["10.1002\/anie.201902405"],"URL":"https:\/\/doi.org\/10.1002\/anie.201902405","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,5,10]]},"assertion":[{"value":"2019-02-23","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2019-05-10","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}