{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,8]],"date-time":"2026-06-08T20:29:20Z","timestamp":1780950560365,"version":"3.54.1"},"reference-count":103,"publisher":"Wiley","issue":"10","license":[{"start":{"date-parts":[[2021,1,15]],"date-time":"2021-01-15T00:00:00Z","timestamp":1610668800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["404194277"],"award-info":[{"award-number":["404194277"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["EXC 2075 - 390740016"],"award-info":[{"award-number":["EXC 2075 - 390740016"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["INST 40\/467-1 FUGG (JUSTUS cluster)"],"award-info":[{"award-number":["INST 40\/467-1 FUGG (JUSTUS cluster)"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004350","name":"Studienstiftung des Deutschen Volkes","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100004350","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":[[2021,3]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Enantiopure secondary alcohols are fundamental high\u2010value synthetic building blocks. One of the most attractive ways to get access to this compound class is the catalytic hydroboration. We describe a new concept for this reaction type that allowed for exceptional catalytic turnover numbers (up to 15\u2009400), which were increased by around 1.5\u20133 orders of magnitude compared to the most active catalysts previously reported. In our concept an aprotic ammonium halide moiety cooperates with an oxophilic Lewis acid within the same catalyst molecule. Control experiments reveal that both catalytic centers are essential for the observed activity. Kinetic, spectroscopic and computational studies show that the hydride transfer is rate limiting and proceeds via a concerted mechanism, in which hydride at Boron is continuously displaced by iodide, reminiscent to an S<jats:sub>N<\/jats:sub>2 reaction. The catalyst, which is accessible in high yields in few steps, was found to be stable during catalysis, readily recyclable and could be reused 10 times still efficiently working.<\/jats:p>","DOI":"10.1002\/anie.202012796","type":"journal-article","created":{"date-parts":[[2020,11,19]],"date-time":"2020-11-19T20:47:06Z","timestamp":1605818826000},"page":"5544-5553","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":23,"title":["Highly Active Cooperative Lewis Acid\u2014Ammonium Salt Catalyst for the Enantioselective Hydroboration of Ketones"],"prefix":"10.1002","volume":"60","author":[{"given":"Marvin","family":"Titze","sequence":"first","affiliation":[{"name":"Universit\u00e4t Stuttgart Institut f\u00fcr Organische Chemie  Pfaffenwaldring 55 70569 Stuttgart Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2285-3381","authenticated-orcid":false,"given":"Juliane","family":"Heitk\u00e4mper","sequence":"additional","affiliation":[{"name":"Universit\u00e4t Stuttgart Institut f\u00fcr Theoretische Chemie  Pfaffenwaldring 55 70569 Stuttgart Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Thorsten","family":"Junge","sequence":"additional","affiliation":[{"name":"Universit\u00e4t Stuttgart Institut f\u00fcr Organische Chemie  Pfaffenwaldring 55 70569 Stuttgart Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6178-7669","authenticated-orcid":false,"given":"Johannes","family":"K\u00e4stner","sequence":"additional","affiliation":[{"name":"Universit\u00e4t Stuttgart Institut f\u00fcr Theoretische Chemie  Pfaffenwaldring 55 70569 Stuttgart Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6668-4017","authenticated-orcid":false,"given":"Ren\u00e9","family":"Peters","sequence":"additional","affiliation":[{"name":"Universit\u00e4t Stuttgart Institut f\u00fcr Organische Chemie  Pfaffenwaldring 55 70569 Stuttgart Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2021,1,15]]},"reference":[{"key":"e_1_2_7_1_1","unstructured":"\u00a0"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20010105)40:1<40::AID-ANIE40>3.0.CO;2-5"},{"key":"e_1_2_7_2_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20010105)113:1<40::AID-ANGE40>3.0.CO;2-K"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1351\/pac200173020227"},{"key":"e_1_2_7_4_2","first-page":"1","volume-title":"New Frontiers in Asymmetric Catalysis","author":"Ohkuma T.","year":"2006"},{"key":"e_1_2_7_5_2","first-page":"59","volume-title":"Science of Synthesis Stereoselective Synthesis, Vol.\u20052","author":"Zaidlewicz M.","year":"2011"},{"key":"e_1_2_7_6_2","unstructured":"N. Arai T. Ohkuma inScience of Synthesis Stereoselective Synthesis Vol.\u20052(Eds.: J.\u2005G. De\u2005Vries G.\u2005A. Molander P.\u2005A. Evans) Thieme Stuttgart 2011 pp.\u20059\u201357;"},{"key":"e_1_2_7_7_2","first-page":"2094","volume-title":"Encyclopedia of Industrial Biotechnology, Vol.\u20053","author":"Gr\u00f6ger H.","year":"2010"},{"key":"e_1_2_7_8_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7CY02409F"},{"key":"e_1_2_7_9_2","doi-asserted-by":"publisher","DOI":"10.1007\/s10295-008-0381-2"},{"key":"e_1_2_7_10_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8RA09004A"},{"key":"e_1_2_7_11_1","unstructured":"Reviews:"},{"key":"e_1_2_7_12_2","doi-asserted-by":"publisher","DOI":"10.1039\/B811341F"},{"key":"e_1_2_7_13_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9CY00807A"},{"key":"e_1_2_7_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar00013a003"},{"key":"e_1_2_7_15_2","first-page":"84","volume-title":"ACS Symposium Series, Vol.\u2005641","author":"Ramachandran P. V.","year":"1996"},{"key":"e_1_2_7_16_1","unstructured":"Reviews on boron chemistry:"},{"key":"e_1_2_7_17_2","first-page":"665","volume":"14","author":"Kaur P.","year":"2016","journal-title":"Curr. Org. Synth."},{"key":"e_1_2_7_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/3527606548.ch1"},{"key":"e_1_2_7_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/bk-2016-1236.ch001"},{"key":"e_1_2_7_20_1","unstructured":"\u00a0"},{"key":"e_1_2_7_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO;2-Z"},{"key":"e_1_2_7_21_3","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3757(19980803)110:15<2092::AID-ANGE2092>3.0.CO;2-M"},{"key":"e_1_2_7_22_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5CC01084E"},{"key":"e_1_2_7_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201704184"},{"key":"e_1_2_7_23_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201704184"},{"key":"e_1_2_7_24_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201806196"},{"key":"e_1_2_7_24_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201806196"},{"key":"e_1_2_7_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b05340"},{"key":"e_1_2_7_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201902188"},{"key":"e_1_2_7_26_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201902188"},{"key":"e_1_2_7_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b10364"},{"key":"e_1_2_7_28_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9CC09111D"},{"key":"e_1_2_7_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c00293"},{"key":"e_1_2_7_30_2","doi-asserted-by":"publisher","DOI":"10.6023\/cjoc202008039"},{"key":"e_1_2_7_31_1","unstructured":"\u00a0"},{"key":"e_1_2_7_32_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200801143"},{"key":"e_1_2_7_32_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200801143"},{"key":"e_1_2_7_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201000840"},{"key":"e_1_2_7_34_2","doi-asserted-by":"publisher","DOI":"10.3390\/molecules17067121"},{"key":"e_1_2_7_35_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6CC09774J"},{"key":"e_1_2_7_36_1","unstructured":"\u00a0"},{"key":"e_1_2_7_37_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201612493"},{"key":"e_1_2_7_37_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201612493"},{"key":"e_1_2_7_38_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201804388"},{"key":"e_1_2_7_39_2","author":"Junge T.","journal-title":"ChemCatChem"},{"key":"e_1_2_7_40_1","doi-asserted-by":"publisher","DOI":"10.1002\/9783527681020"},{"key":"e_1_2_7_41_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.9b00262"},{"key":"e_1_2_7_42_1","unstructured":"Selected related polyfunctional catalysts developed by our group:"},{"key":"e_1_2_7_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202009093"},{"key":"e_1_2_7_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b04902"},{"key":"e_1_2_7_45_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201814453"},{"key":"e_1_2_7_45_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201814453"},{"key":"e_1_2_7_46_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201502930"},{"key":"e_1_2_7_46_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201502930"},{"key":"e_1_2_7_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.organomet.7b00729"},{"key":"e_1_2_7_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/om500762r"},{"key":"e_1_2_7_49_2","doi-asserted-by":"publisher","DOI":"10.1021\/om3008629"},{"key":"e_1_2_7_50_1","unstructured":"Non-enantioselective Al-catalyzed hydroboration of ketones:"},{"key":"e_1_2_7_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.organomet.8b00933"},{"key":"e_1_2_7_52_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6b02310"},{"key":"e_1_2_7_53_2","doi-asserted-by":"publisher","DOI":"10.1002\/zaac.201600313"},{"key":"e_1_2_7_54_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7CC08214B"},{"key":"e_1_2_7_55_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201801541"},{"key":"e_1_2_7_56_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201503304"},{"key":"e_1_2_7_56_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201503304"},{"key":"e_1_2_7_57_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201609690"},{"key":"e_1_2_7_57_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201609690"},{"key":"e_1_2_7_58_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.oprd.9b00205"},{"key":"e_1_2_7_59_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.7b02460"},{"key":"e_1_2_7_60_1","unstructured":"Under these conditions we also investigated the use of the correspondingC2-symmetric ligand bearing two ammonium moieties. However both yield (11\u2009%) andee(18\u2009%) were poor."},{"key":"e_1_2_7_61_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-1995-5191"},{"key":"e_1_2_7_62_1","unstructured":"\u00a0"},{"key":"e_1_2_7_63_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20020802)41:15<2781::AID-ANIE2781>3.0.CO;2-S"},{"key":"e_1_2_7_63_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20020802)114:15<2905::AID-ANGE2905>3.0.CO;2-C"},{"key":"e_1_2_7_64_2","doi-asserted-by":"publisher","DOI":"10.1039\/c4sc00075g"},{"key":"e_1_2_7_65_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja017434u"},{"key":"e_1_2_7_66_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201901514"},{"key":"e_1_2_7_67_1","unstructured":"Deposition Number 2030886contains 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 servicewww.ccdc.cam.ac.uk\/structures."},{"key":"e_1_2_7_68_1","unstructured":"\u00a0"},{"key":"e_1_2_7_69_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja980299"},{"key":"e_1_2_7_70_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja991621z"},{"key":"e_1_2_7_71_1","unstructured":"\u00a0"},{"key":"e_1_2_7_72_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja207634t"},{"key":"e_1_2_7_73_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b05841"},{"key":"e_1_2_7_74_1","unstructured":"[iPrOH] determined by1H-NMR for experiment 1 in Table\u20058 after 50\u2009% conversion is in good agreement with the calculated value used in Table\u20058."},{"key":"e_1_2_7_75_1","unstructured":"\u00a0"},{"key":"e_1_2_7_76_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201609757"},{"key":"e_1_2_7_76_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201609757"},{"key":"e_1_2_7_77_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8SC04698K"},{"key":"e_1_2_7_78_1","unstructured":"Also for catalystC4lacking an onium moiety a first order kinetic dependence was found."},{"key":"e_1_2_7_79_1","unstructured":"For the BPin ester of2\u2009a no accelerating effect was found."},{"key":"e_1_2_7_80_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200705241"},{"key":"e_1_2_7_80_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200705241"},{"key":"e_1_2_7_81_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp9028968"},{"key":"e_1_2_7_82_1","doi-asserted-by":"publisher","DOI":"10.1002\/wcms.1163"},{"key":"e_1_2_7_83_1","unstructured":"\u201cTURBOMOLE V7 2015 a development of the University of Karlsruhe and Forschungszentrum Karlsruhe GmbH 1989\u20132007 TURBOMOLE GmbH since 2007; can be found underhttp:\/\/www.turbomole.com."},{"key":"e_1_2_7_84_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00214-007-0310-x"},{"key":"e_1_2_7_85_1","unstructured":"\u00a0"},{"key":"e_1_2_7_86_2","doi-asserted-by":"publisher","DOI":"10.1039\/b508541a"},{"key":"e_1_2_7_87_2","doi-asserted-by":"publisher","DOI":"10.1039\/b515623h"},{"key":"e_1_2_7_88_1","doi-asserted-by":"publisher","DOI":"10.1039\/P29930000799"},{"key":"e_1_2_7_89_1","doi-asserted-by":"publisher","DOI":"10.1021\/ct400687b"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202012796","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202012796","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202012796","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,8,27]],"date-time":"2023-08-27T16:17:43Z","timestamp":1693153063000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202012796"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,1,15]]},"references-count":103,"journal-issue":{"issue":"10","published-print":{"date-parts":[[2021,3]]}},"alternative-id":["10.1002\/anie.202012796"],"URL":"https:\/\/doi.org\/10.1002\/anie.202012796","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,1,15]]},"assertion":[{"value":"2020-09-21","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2021-01-15","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}