{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,13]],"date-time":"2026-03-13T12:22:50Z","timestamp":1773404570705,"version":"3.50.1"},"reference-count":30,"publisher":"Wiley","issue":"23","license":[{"start":{"date-parts":[[2016,7,21]],"date-time":"2016-07-21T00:00:00Z","timestamp":1469059200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["UID\/QUI\/00062\/2013"],"award-info":[{"award-number":["UID\/QUI\/00062\/2013"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["UID\/CTM\/50011\/2013"],"award-info":[{"award-number":["UID\/CTM\/50011\/2013"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["SFRH\/BD\/76407\/2011"],"award-info":[{"award-number":["SFRH\/BD\/76407\/2011"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["SFRH\/BD\/84231\/2012"],"award-info":[{"award-number":["SFRH\/BD\/84231\/2012"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Eur J Org Chem"],"published-print":{"date-parts":[[2016,8]]},"abstract":"<jats:p>A one\u2010pot diastereoselective base\u2010catalyzed Michael\u2010initiated ring\u2010closure (MIRC) of activated methyl ketones with 3\u2010bromochromones to give cyclopropa[<jats:italic>b<\/jats:italic>]chromanones is described. Three asymmetric centres are generated in the new cyclopropa[<jats:italic>b<\/jats:italic>]chromanone skeleton. Stereochemistry studies based on NMR spectroscopy and single\u2010crystal X\u2010ray diffraction analysis revealed the <jats:italic>trans<\/jats:italic> configuration of the cyclopropane ring, with the (1<jats:italic>R<\/jats:italic>,1a<jats:italic>S<\/jats:italic>,7a<jats:italic>R<\/jats:italic>)\/(1<jats:italic>S<\/jats:italic>,1a<jats:italic>R<\/jats:italic>,7a<jats:italic>S<\/jats:italic>) pair of enantiomers, as was further confirmed by chiral HPLC. The use of acetone in our reaction produced a 1\u2010acetyl\u2010substituted cyclopropa[<jats:italic>b<\/jats:italic>]chromanone that can undergo a subsequent MIRC reaction with a second molecule of 3\u2010bromochromone to give the first described 1,1\u2032\u2010carbonylbis(cyclopropa[<jats:italic>b<\/jats:italic>]chromanone) dimers as a <jats:italic>meso<\/jats:italic> form.<\/jats:p>","DOI":"10.1002\/ejoc.201600413","type":"journal-article","created":{"date-parts":[[2016,7,21]],"date-time":"2016-07-21T05:59:37Z","timestamp":1469080777000},"page":"3949-3958","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Catalytic One\u2010Pot Diastereoselective Michael\u2010Initiated Ring\u2010Closure of Methyl Ketones with 3\u2010Bromochromones: Synthesis of Cyclopropa[<i>b<\/i>]chromanones"],"prefix":"10.1002","volume":"2016","author":[{"given":"Joana L. C.","family":"Sousa","sequence":"first","affiliation":[{"name":"QOPNA Department of Chemistry University of Aveiro 3810\u2010193 Aveiro Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4064-3310","authenticated-orcid":false,"given":"Oualid","family":"Talhi","sequence":"additional","affiliation":[{"name":"QOPNA Department of Chemistry University of Aveiro 3810\u2010193 Aveiro Portugal"},{"name":"Centre de Recherche Scientifique et Technique en Analyses Physico\u2010Chimiques CRAPC BP384 42004 Bou\u2010Ismail Tipaza Algeria"}]},{"given":"Ricardo F.","family":"Mendes","sequence":"additional","affiliation":[{"name":"CICECO \u2013 Aveiro Institute of Materials Department of Chemistry University of Aveiro 3810\u2010193 Aveiro Portugal"}]},{"given":"Filipe A.","family":"Almeida Paz","sequence":"additional","affiliation":[{"name":"CICECO \u2013 Aveiro Institute of Materials Department of Chemistry University of Aveiro 3810\u2010193 Aveiro Portugal"}]},{"given":"Khaldoun","family":"Bachari","sequence":"additional","affiliation":[{"name":"Centre de Recherche Scientifique et Technique en Analyses Physico\u2010Chimiques CRAPC BP384 42004 Bou\u2010Ismail Tipaza Algeria"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2861-8286","authenticated-orcid":false,"given":"Artur M. S.","family":"Silva","sequence":"additional","affiliation":[{"name":"QOPNA Department of Chemistry University of Aveiro 3810\u2010193 Aveiro Portugal"}]}],"member":"311","published-online":{"date-parts":[[2016,7,21]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1039\/c4np00008k"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2cs35067j"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2008.04.079"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2015.08.056"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm500537u"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5b01216"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2013.10.018"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2015.01.060"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201403077"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4CC09844G"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol500267w"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo902618e"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo030312v"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/ie201178d"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol9005882"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja908075u"},{"key":"e_1_2_6_18_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4OB00087K"},{"key":"e_1_2_6_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo070444e"},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2005.10.167"},{"key":"e_1_2_6_21_1","doi-asserted-by":"crossref","first-page":"91","DOI":"10.3998\/ark.5550190.0003.610","author":"Casey M.","year":"2002","journal-title":"ARKIVOC"},{"key":"e_1_2_6_22_1","doi-asserted-by":"publisher","DOI":"10.2174\/15701794113109990063"},{"key":"e_1_2_6_23_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0035-1560580"},{"key":"e_1_2_6_24_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200900026"},{"key":"e_1_2_6_25_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201501278"},{"key":"e_1_2_6_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr400265z"},{"key":"e_1_2_6_27_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201309886"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201309886"},{"key":"e_1_2_6_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol503246k"},{"key":"e_1_2_6_29_1","doi-asserted-by":"publisher","DOI":"10.1039\/b004422i"},{"key":"e_1_2_6_30_1","doi-asserted-by":"publisher","DOI":"10.1039\/p19870002597"}],"container-title":["European Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fejoc.201600413","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/ejoc.201600413","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,15]],"date-time":"2025-10-15T19:07:06Z","timestamp":1760555226000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/ejoc.201600413"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2016,7,21]]},"references-count":30,"journal-issue":{"issue":"23","published-print":{"date-parts":[[2016,8]]}},"alternative-id":["10.1002\/ejoc.201600413"],"URL":"https:\/\/doi.org\/10.1002\/ejoc.201600413","archive":["Portico"],"relation":{},"ISSN":["1434-193X","1099-0690"],"issn-type":[{"value":"1434-193X","type":"print"},{"value":"1099-0690","type":"electronic"}],"subject":[],"published":{"date-parts":[[2016,7,21]]},"assertion":[{"value":"2016-04-03","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2016-07-21","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}