{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,15]],"date-time":"2026-10-15T03:00:59Z","timestamp":1792033259291,"version":"4.4.0"},"reference-count":53,"publisher":"Wiley","issue":"19","license":[{"start":{"date-parts":[[2021,3,5]],"date-time":"2021-03-05T00:00:00Z","timestamp":1614902400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100000266","name":"Engineering and Physical Sciences Research Council","doi-asserted-by":"publisher","award":["EP\/S513854\/1"],"award-info":[{"award-number":["EP\/S513854\/1"]}],"id":[{"id":"10.13039\/501100000266","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100004325","name":"AstraZeneca","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100004325","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000837","name":"University of Nottingham","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100000837","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100004330","name":"GlaxoSmithKline","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100004330","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2021,4]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Domino reactions involving nickel\u2010catalyzed additions of (hetero)arylboronic acids to alkynes, followed by cyclization of the alkenylnickel intermediates onto tethered acyclic ketones to give chiral tertiary\u2010alcohol\u2010containing products in high enantioselectivities, are described. The reversible <jats:italic>E<\/jats:italic>\/<jats:italic>Z<\/jats:italic> isomerization of the alkenylnickel intermediates enables overall <jats:italic>anti<\/jats:italic>\u2010arylmetallative cyclization to occur. The ring system of the products are substructures of certain diarylindolizidine alkaloids.<\/jats:p>","DOI":"10.1002\/chem.202100143","type":"journal-article","created":{"date-parts":[[2021,2,5]],"date-time":"2021-02-05T09:30:58Z","timestamp":1612517458000},"page":"5897-5900","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":35,"title":["Enantioselective Nickel\u2010Catalyzed <i>anti<\/i>\u2010Arylmetallative Cyclizations onto Acyclic Ketones"],"prefix":"10.1002","volume":"27","author":[{"given":"Harley","family":"Green","sequence":"first","affiliation":[{"name":"The GlaxoSmithKline Carbon Neutral Laboratories for, Sustainable Chemistry University of Nottingham  Jubilee Campus, Triumph Road Nottingham NG7 2TU UK"},{"name":"School of Chemistry University of Nottingham  University Park Nottingham NG7 2RD UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3461-9675","authenticated-orcid":false,"given":"Stephen P.","family":"Argent","sequence":"additional","affiliation":[{"name":"School of Chemistry University of Nottingham  University Park Nottingham NG7 2RD UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7543-256X","authenticated-orcid":false,"given":"Hon Wai","family":"Lam","sequence":"additional","affiliation":[{"name":"The GlaxoSmithKline Carbon Neutral Laboratories for, Sustainable Chemistry University of Nottingham  Jubilee Campus, Triumph Road Nottingham NG7 2TU UK"},{"name":"School of Chemistry University of Nottingham  University Park Nottingham NG7 2RD UK"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2021,3,5]]},"reference":[{"key":"e_1_2_2_1_1","unstructured":"For selected general reviews on the enantioselective synthesis of tertiary alcohols via nucleophilic additions to ketones see:"},{"key":"e_1_2_2_2_2","first-page":"1647","author":"Hatano M.","year":"2008","journal-title":"Synthesis"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr078340r"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200900166"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.5b02832"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201503412"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7CS00824D"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201801023"},{"key":"e_1_2_2_9_1","unstructured":"For representative examples see:"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja044021v"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200500843"},{"key":"e_1_2_2_11_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200500843"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0711772"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol500993h"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9SC06309A"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c00638"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol902538n"},{"key":"e_1_2_2_17_1","unstructured":"\u00a0"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b04206"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201703380"},{"key":"e_1_2_2_19_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201703380"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201805578"},{"key":"e_1_2_2_20_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201805578"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c02075"},{"key":"e_1_2_2_22_1","unstructured":"\u00a0"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6SC01191H"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7CC08408K"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8CC06649C"},{"key":"e_1_2_2_26_1","unstructured":"For reviews on nickel-catalyzed difunctionalization of alkynes see:"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0040-1707885"},{"key":"e_1_2_2_28_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0QO01097A"},{"key":"e_1_2_2_29_1","unstructured":"\u00a0"},{"key":"e_1_2_2_30_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6CC10256E"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.8b02618"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201909015"},{"key":"e_1_2_2_32_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201909015"},{"key":"e_1_2_2_33_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9QO01266D"},{"key":"e_1_2_2_34_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-020-15837-1"},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c02534"},{"key":"e_1_2_2_36_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0SC04173D"},{"key":"e_1_2_2_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c10055"},{"key":"e_1_2_2_38_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo400342y"},{"key":"e_1_2_2_39_1","doi-asserted-by":"publisher","DOI":"10.1071\/CH9892243"},{"key":"e_1_2_2_40_1","unstructured":"For examples of the synthesis of (\u2212)-septicine see:"},{"key":"e_1_2_2_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo9711495"},{"key":"e_1_2_2_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol403229q"},{"key":"e_1_2_2_43_1","unstructured":"\u00a0"},{"key":"e_1_2_2_44_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.phytol.2015.12.007"},{"key":"e_1_2_2_45_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2018.01.032"},{"key":"e_1_2_2_46_1","unstructured":"The absolute configurations of products2\u2009fand2\u2009jwere determined by X-ray crystallography and those of the remaining products were assigned by analogy. Deposition number\u20052040015contains the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum KarlsruheAccess Structures service."},{"key":"e_1_2_2_47_1","unstructured":"Cyclopenten-2-one6\u2009awas accompanied by inseparable unidentified impurities and the yield was therefore determined by1H\u2005NMR analysis using an internal standard."},{"key":"e_1_2_2_48_1","unstructured":"Because of the loweevalue of6\u2009b the assignment of its absolute configuration which was made by analogy to the results reported in ref.\u2005[3c] is tentative."},{"key":"e_1_2_2_49_1","unstructured":"The research data associated with this publication can be found at:https:\/\/doi.org\/10.17639\/nott.7098."}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202100143","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chem.202100143","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202100143","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T15:56:55Z","timestamp":1760284615000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202100143"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,3,5]]},"references-count":53,"journal-issue":{"issue":"19","published-print":{"date-parts":[[2021,4]]}},"alternative-id":["10.1002\/chem.202100143"],"URL":"https:\/\/doi.org\/10.1002\/chem.202100143","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,3,5]]},"assertion":[{"value":"2021-01-13","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2021-03-05","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}