{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,7]],"date-time":"2026-03-07T10:33:04Z","timestamp":1772879584936,"version":"3.50.1"},"reference-count":63,"publisher":"Wiley","issue":"3","license":[{"start":{"date-parts":[[2024,11,7]],"date-time":"2024-11-07T00:00:00Z","timestamp":1730937600000},"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":["2022.04623.PTDC"],"award-info":[{"award-number":["2022.04623.PTDC"]}],"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":["UIDB\/00100\/2020"],"award-info":[{"award-number":["UIDB\/00100\/2020"]}],"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":["UIDP\/00100\/2020"],"award-info":[{"award-number":["UIDP\/00100\/2020"]}],"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":["LA\/P\/0056\/2020"],"award-info":[{"award-number":["LA\/P\/0056\/2020"]}],"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":["UIDB\/04138\/2020"],"award-info":[{"award-number":["UIDB\/04138\/2020"]}],"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":["UIDP\/04138\/2020"],"award-info":[{"award-number":["UIDP\/04138\/2020"]}],"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":["2020\/02383\/CEECIND"],"award-info":[{"award-number":["2020\/02383\/CEECIND"]}],"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":["2020\/06352\/BD"],"award-info":[{"award-number":["2020\/06352\/BD"]}],"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":["2023.01672.BD"],"award-info":[{"award-number":["2023.01672.BD"]}],"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":["ChemSusChem"],"published-print":{"date-parts":[[2025,2]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Sparteine is widely used as a chiral ligand in asymmetric synthesis, but methods for providing efficient access to functionalized sparteine derivatives are still limited. Herein, we describe an electrochemical \u03b1\u2010cyanation of sparteine\u2010type bis\u2010quinolizidine alkaloids. This method features commercially available setups for batch and single\u2010pass continuous flow conditions, enabling easy gram scale synthesis of valuable racemic and enantiopure products. Moreover, insights into the selectivity of the reaction and overoxidation mechanisms are disclosed. This allows for the development of divergent oxidation pathways depending on the electrolysis conditions.<\/jats:p>","DOI":"10.1002\/cssc.202401305","type":"journal-article","created":{"date-parts":[[2024,9,21]],"date-time":"2024-09-21T05:26:49Z","timestamp":1726896409000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Electrooxidative C(sp<sup>3<\/sup>)\u2212H Cyanation of Sparteine and Lupanine in Undivided Batch and Continuous\u2010Flow Cells"],"prefix":"10.1002","volume":"18","author":[{"given":"Raquel M.","family":"Dur\u00e3o","sequence":"first","affiliation":[{"name":"Research Institute for Medicines (iMed.ULisboa) Faculty of Pharmacy University of Lisbon  Av. Prof. Gama Pinto Lisbon 1649-003 Portugal"}]},{"given":"Duarte B.","family":"Clemente","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural, Institute of Molecular Sciences Faculty of Sciences University of Lisbon  Campo Grande Lisbon 1749-016 Portugal"}]},{"given":"Abdullahi A.","family":"Muiz","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural, Institute of Molecular Sciences Faculty of Sciences University of Lisbon  Campo Grande Lisbon 1749-016 Portugal"}]},{"given":"Sara","family":"Lima","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural, Institute of Molecular Sciences Faculty of Sciences University of Lisbon  Campo Grande Lisbon 1749-016 Portugal"}]},{"given":"Daniel F.","family":"Carvalho","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural, Institute of Molecular Sciences Faculty of Sciences University of Lisbon  Campo Grande Lisbon 1749-016 Portugal"}]},{"given":"Stijn","family":"De Vos","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural, Institute of Molecular Sciences Faculty of Sciences University of Lisbon  Campo Grande Lisbon 1749-016 Portugal"}]},{"given":"Rita","family":"de Jesus","sequence":"additional","affiliation":[{"name":"Research Institute for Medicines (iMed.ULisboa) Faculty of Pharmacy University of Lisbon  Av. Prof. Gama Pinto Lisbon 1649-003 Portugal"},{"name":"Current address: Otto-Diels-Institut f\u00fcr Organische Chemie Christian-Albrechts-Universit\u00e4t zu Kiel  Otto-Hahn-Platz\u20054 24118 Kiel Germany"}]},{"given":"Andreia","family":"Fortuna","sequence":"additional","affiliation":[{"name":"Research Institute for Medicines (iMed.ULisboa) Faculty of Pharmacy University of Lisbon  Av. Prof. Gama Pinto Lisbon 1649-003 Portugal"},{"name":"Current address: BioISI\u2013BioSystems and Integrative Sciences Institute Faculty of Sciences University of Lisbon Campo Grande  Lisbon 1749-016 Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7284-5948","authenticated-orcid":false,"given":"Carlos A. M.","family":"Afonso","sequence":"additional","affiliation":[{"name":"Research Institute for Medicines (iMed.ULisboa) Faculty of Pharmacy University of Lisbon  Av. Prof. Gama Pinto Lisbon 1649-003 Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7459-0993","authenticated-orcid":false,"given":"Jaime A. S.","family":"Coelho","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural, Institute of Molecular Sciences Faculty of Sciences University of Lisbon  Campo Grande Lisbon 1749-016 Portugal"}]}],"member":"311","published-online":{"date-parts":[[2024,11,7]]},"reference":[{"key":"e_1_2_7_1_1","unstructured":"Deposition numbers 2346974 (for7) and 2346976 (for9) contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service."},{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-2003-38760"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1007\/b136348"},{"key":"e_1_2_7_4_1","first-page":"1","volume-title":"Encyclopedia of Reagents for Organic Synthesis (EROS)","author":"Hoppe D.","year":"2007"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.3389\/fpls.2012.00239"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/cmdc.201700568"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja027774v"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2016.09.001"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol800109s"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/tcr.202000066"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1039\/a908290e"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4020(78)80175-6"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)97719-0"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(98)02184-4"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201504845"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1135\/cccc20042068"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja109617y"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00395a029"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.3762\/bjoc.10.323"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00438a005"},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.199719970137"},{"key":"e_1_2_7_22_1","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.199719971011"},{"key":"e_1_2_7_23_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202302664"},{"key":"e_1_2_7_24_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1OB01416A"},{"key":"e_1_2_7_25_1","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.202300807"},{"key":"e_1_2_7_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b08145"},{"key":"e_1_2_7_27_1","doi-asserted-by":"publisher","DOI":"10.1039\/B816598J"},{"key":"e_1_2_7_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja804048a"},{"key":"e_1_2_7_29_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5QO00075K"},{"key":"e_1_2_7_30_1","doi-asserted-by":"publisher","DOI":"10.1186\/s40508-016-0051-z"},{"key":"e_1_2_7_31_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6GC00611F"},{"key":"e_1_2_7_32_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5GC01008J"},{"key":"e_1_2_7_33_1","doi-asserted-by":"publisher","DOI":"10.1201\/9781420032079"},{"key":"e_1_2_7_34_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.9b00412"},{"key":"e_1_2_7_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.7b00360"},{"key":"e_1_2_7_36_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.isci.2020.101720"},{"key":"e_1_2_7_37_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9EE00219G"},{"key":"e_1_2_7_38_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c02018"},{"key":"e_1_2_7_39_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3OB00313B"},{"key":"e_1_2_7_40_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8OB00063H"},{"key":"e_1_2_7_41_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b00021"},{"key":"e_1_2_7_42_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.3c00147"},{"key":"e_1_2_7_43_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-0728(69)80107-5"},{"key":"e_1_2_7_44_1","unstructured":"N. Maulide B. Peng C.\u2005A.\u2005M. Afonso R.\u2005F.\u2005M. Frade (Studiengesellschaft Kohle mbH Universidade de Lisboa) Eur. Pat. No. EP2808326\u2005A1 2014."},{"key":"e_1_2_7_45_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201712852"},{"key":"e_1_2_7_46_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja109617y"},{"key":"e_1_2_7_47_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0957-4166(01)00234-8"},{"key":"e_1_2_7_48_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molstruc.2004.10.034"},{"key":"e_1_2_7_49_1","doi-asserted-by":"publisher","DOI":"10.1107\/S0021889812029111"},{"key":"e_1_2_7_50_1","doi-asserted-by":"publisher","DOI":"10.1107\/S002188980600731X"},{"key":"e_1_2_7_51_1","unstructured":"M.\u2005J. Frisch G.\u2005W. Trucks H.\u2005B. Schlegel G.\u2005E. Scuseria M.\u2005A. Robb J.\u2005R. Cheeseman G. Scalmani V. Barone G.\u2005A. Petersson H. Nakatsuji X. Li M. Caricato A.\u2005V. Marenich J. Bloino B.\u2005G. Janesko R. Gomperts B. Mennucci H.\u2005P. Hratchian J.\u2005V. Ortiz A.\u2005F. Izmaylov J.\u2005L. Sonnenberg D. Williams-Young F. Ding F. Lipparini F. Egidi J. Goings B. Peng A. Petrone T. Henderson D. Ranasinghe V.\u2005G. Zakrzewski J. Gao N. Rega G. Zheng W. Liang M. Hada M. Ehara K. Toyota R. Fukuda J. Hasegawa M. Ishida T. Nakajima Y. Honda O. Kitao H. Nakai T. Vreven K. Throssell J.\u2005A. Montgomery(Jr.) J.\u2005E. Peralta F. Ogliaro M.\u2005J. Bearpark J.\u2005J. Heyd E.\u2005N. Brothers K.\u2005N. Kudin V.\u2005N. Staroverov T.\u2005A. Keith R. Kobayashi J. Normand K. Raghavachari A.\u2005P. Rendell J.\u2005C. Burant S.\u2005S. Iyengar J. Tomasi M. Cossi J.\u2005M. Millam M. Klene C. Adamo R. Cammi J.\u2005W. Ochterski R.\u2005L. Martin K. Morokuma O. Farkas J.\u2005B. Foresman D.\u2005J. Fox Gaussian 16 (Revision C.01) Gaussian Inc. Wallingford CT 2019."},{"key":"e_1_2_7_52_1","unstructured":"CYLview20; C.\u2005Y. Legault Universit\u00e9 de Sherbrooke 2020(http:\/\/www.cylview.org)."},{"key":"e_1_2_7_53_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00214-007-0310-x"},{"key":"e_1_2_7_54_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.474659"},{"key":"e_1_2_7_55_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0009-2614(98)00106-7"},{"key":"e_1_2_7_56_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.473558"},{"key":"e_1_2_7_57_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr9904009"},{"key":"e_1_2_7_58_1","first-page":"714","volume":"27","author":"Roth H. G.","year":"2016","journal-title":"Synlett"},{"key":"e_1_2_7_59_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo2017982"},{"key":"e_1_2_7_60_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jechem.2022.03.024"},{"key":"e_1_2_7_61_1","first-page":"51","volume":"55","author":"Navarro R. M.","year":"2011","journal-title":"J. Mex. Chem. Soc."},{"key":"e_1_2_7_62_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja0171759"},{"key":"e_1_2_7_63_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules191016190"}],"container-title":["ChemSusChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cssc.202401305","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T19:47:12Z","timestamp":1760384832000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/cssc.202401305"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,11,7]]},"references-count":63,"journal-issue":{"issue":"3","published-print":{"date-parts":[[2025,2]]}},"alternative-id":["10.1002\/cssc.202401305"],"URL":"https:\/\/doi.org\/10.1002\/cssc.202401305","archive":["Portico"],"relation":{},"ISSN":["1864-5631","1864-564X"],"issn-type":[{"value":"1864-5631","type":"print"},{"value":"1864-564X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,11,7]]},"assertion":[{"value":"2024-06-19","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2024-11-07","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202401305"}}