{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T16:04:48Z","timestamp":1787069088584,"version":"build-2736575974"},"reference-count":119,"publisher":"Wiley","issue":"1","license":[{"start":{"date-parts":[[2022,11,29]],"date-time":"2022-11-29T00:00:00Z","timestamp":1669680000000},"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","id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100005722","name":"Ludwig-Maximilians-Universit\u00e4t M\u00fcnchen","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100005722","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":[[2023,1,2]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    We report a practical in situ quench (ISQ) procedure involving the generation of chiral secondary alkyllithiums from secondary alkyl iodides (including functionalized iodides bearing an ester or a nitrile) in the presence of various electrophiles such as aldehydes, ketones, Weinreb amides, isocyanates, sulfides, or boronates. This ISQ\u2010reaction allowed the preparation of a broad range of optically enriched ketones, alcohols, amides, sulfides and boronic acid esters in typically 90\u201398\u2009%\n                    <jats:italic>ee<\/jats:italic>\n                    . Remarkably, these reactions were performed at \u221278\u2009\u00b0C or \u221240\u2009\u00b0C in batch. A continuous flow set\u2010up permitted reaction temperatures between \u221220\u2009\u00b0C and 0\u2009\u00b0C and allowed a scale\u2010up up to a 40\u2010fold without further optimization.\n                  <\/jats:p>","DOI":"10.1002\/anie.202214377","type":"journal-article","created":{"date-parts":[[2022,10,21]],"date-time":"2022-10-21T08:55:05Z","timestamp":1666342505000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":12,"title":["In Situ Quench Reactions of Enantioenriched Secondary Alkyllithium Reagents in Batch and Continuous Flow Using an I\/Li\u2010Exchange"],"prefix":"10.1002","volume":"62","author":[{"given":"Alexander","family":"Kremsmair","sequence":"first","affiliation":[{"name":"Department Chemie Ludwig-Maximilians-Universit\u00e4t M\u00fcnchen  Butenandtstrasse 5\u201313, Haus F 81377 M\u00fcnchen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Henrik R.","family":"Wilke","sequence":"additional","affiliation":[{"name":"Department Chemie Ludwig-Maximilians-Universit\u00e4t M\u00fcnchen  Butenandtstrasse 5\u201313, Haus F 81377 M\u00fcnchen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Johannes H.","family":"Harenberg","sequence":"additional","affiliation":[{"name":"Department Chemie Ludwig-Maximilians-Universit\u00e4t M\u00fcnchen  Butenandtstrasse 5\u201313, Haus F 81377 M\u00fcnchen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Benjamin R. G.","family":"Bissinger","sequence":"additional","affiliation":[{"name":"Department Chemie Ludwig-Maximilians-Universit\u00e4t M\u00fcnchen  Butenandtstrasse 5\u201313, Haus F 81377 M\u00fcnchen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Matthias M.","family":"Simon","sequence":"additional","affiliation":[{"name":"Department Chemie Ludwig-Maximilians-Universit\u00e4t M\u00fcnchen  Butenandtstrasse 5\u201313, Haus F 81377 M\u00fcnchen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nurtalya","family":"Alandini","sequence":"additional","affiliation":[{"name":"Department Chemie Ludwig-Maximilians-Universit\u00e4t M\u00fcnchen  Butenandtstrasse 5\u201313, Haus F 81377 M\u00fcnchen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7913-4332","authenticated-orcid":false,"given":"Paul","family":"Knochel","sequence":"additional","affiliation":[{"name":"Department Chemie Ludwig-Maximilians-Universit\u00e4t M\u00fcnchen  Butenandtstrasse 5\u201313, Haus F 81377 M\u00fcnchen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2022,11,29]]},"reference":[{"key":"e_1_2_3_1_1","unstructured":"\u00a0"},{"key":"e_1_2_3_2_2","doi-asserted-by":"publisher","DOI":"10.1038\/nrd1798"},{"key":"e_1_2_3_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200504212"},{"key":"e_1_2_3_3_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200504212"},{"key":"e_1_2_3_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/ed1003806"},{"key":"e_1_2_3_5_2","first-page":"1","volume":"1","author":"Cossy J. R.","year":"2012","journal-title":"Compr. Chirality"},{"key":"e_1_2_3_6_2","doi-asserted-by":"publisher","DOI":"10.1002\/ps.5052"},{"key":"e_1_2_3_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/acschemneuro.9b00112"},{"key":"e_1_2_3_8_1","unstructured":"\u00a0"},{"key":"e_1_2_3_9_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20000901)39:17<3072::AID-ANIE3072>3.0.CO;2-4"},{"key":"e_1_2_3_9_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20000901)112:17<3206::AID-ANGE3206>3.0.CO;2-J"},{"key":"e_1_2_3_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20020301)41:5<716::AID-ANIE716>3.0.CO;2-Z"},{"key":"e_1_2_3_10_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20020301)114:5<740::AID-ANGE740>3.0.CO;2-R"},{"key":"e_1_2_3_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/9783906390628"},{"key":"e_1_2_3_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr500715t"},{"key":"e_1_2_3_13_1","unstructured":"\u00a0"},{"key":"e_1_2_3_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00523a066"},{"key":"e_1_2_3_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00180a062"},{"key":"e_1_2_3_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00129a038"},{"key":"e_1_2_3_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199722821"},{"key":"e_1_2_3_17_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19971092105"},{"key":"e_1_2_3_18_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0028-1083280"},{"key":"e_1_2_3_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja4033956"},{"key":"e_1_2_3_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja01166a538"},{"key":"e_1_2_3_21_1","unstructured":"For recent examples of stabilized oxygen-bearing lithium compounds see:"},{"key":"e_1_2_3_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200702146"},{"key":"e_1_2_3_22_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200702146"},{"key":"e_1_2_3_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo101218z"},{"key":"e_1_2_3_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar5002473"},{"key":"e_1_2_3_25_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.2010"},{"key":"e_1_2_3_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.201802815"},{"key":"e_1_2_3_27_1","unstructured":"The addition oft-BuLi to an alkyl iodide produces first an ate-intermediate [Alk-I-t-Bu]\u2212Li+which then collapses to the alkyllithium species. Although conceivable it is unlikely that this high energy intermediate plays a role in reactions with electrophiles. See:"},{"key":"e_1_2_3_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00299a070"},{"key":"e_1_2_3_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00269a055"},{"key":"e_1_2_3_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00191a060"},{"key":"e_1_2_3_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr400187u"},{"key":"e_1_2_3_32_1","unstructured":"For transmetalations to alkylcoppers see:"},{"key":"e_1_2_3_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201505740"},{"key":"e_1_2_3_33_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201505740"},{"key":"e_1_2_3_34_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201601911"},{"key":"e_1_2_3_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b00699"},{"key":"e_1_2_3_36_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201800792"},{"key":"e_1_2_3_36_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201800792"},{"key":"e_1_2_3_37_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9SC05982B"},{"key":"e_1_2_3_38_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202002297"},{"key":"e_1_2_3_39_1","unstructured":"For transmetalations to mixed alkylcopper-zinc reagents see"},{"key":"e_1_2_3_40_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201811330"},{"key":"e_1_2_3_40_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201811330"},{"key":"e_1_2_3_41_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0039-1690766"},{"key":"e_1_2_3_42_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201910397"},{"key":"e_1_2_3_42_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201910397"},{"key":"e_1_2_3_43_1","unstructured":"\u00a0"},{"key":"e_1_2_3_44_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201204076"},{"key":"e_1_2_3_45_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201308679"},{"key":"e_1_2_3_45_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201308679"},{"key":"e_1_2_3_46_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201409165"},{"key":"e_1_2_3_46_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201409165"},{"key":"e_1_2_3_47_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0039-1690713"},{"key":"e_1_2_3_48_1","unstructured":"\u00a0"},{"key":"e_1_2_3_49_2","doi-asserted-by":"publisher","DOI":"10.1007\/978-3-642-85019-6"},{"key":"e_1_2_3_50_2","first-page":"1361","author":"Goto S.","year":"2008","journal-title":"Synlett"},{"key":"e_1_2_3_51_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201403688"},{"key":"e_1_2_3_51_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201403688"},{"key":"e_1_2_3_52_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1SC05315A"},{"key":"e_1_2_3_53_1","unstructured":"For further information see Supporting Information."},{"key":"e_1_2_3_54_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00170a070"},{"key":"e_1_2_3_55_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2007.07.022"},{"key":"e_1_2_3_56_1","unstructured":"\u00a0"},{"key":"e_1_2_3_57_2","first-page":"135","volume":"41","author":"Lipshutz B. H.","year":"1992","journal-title":"Org. React."},{"key":"e_1_2_3_58_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1987.2017"},{"key":"e_1_2_3_59_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201805770"},{"key":"e_1_2_3_59_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201805770"},{"key":"e_1_2_3_60_1","unstructured":"\u00a0"},{"key":"e_1_2_3_61_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0GC02404J"},{"key":"e_1_2_3_62_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscentsci.0c01413"},{"key":"e_1_2_3_63_1","unstructured":"\u00a0"},{"key":"e_1_2_3_64_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201006618"},{"key":"e_1_2_3_64_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201006618"},{"key":"e_1_2_3_65_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol2010006"},{"key":"e_1_2_3_66_2","doi-asserted-by":"publisher","DOI":"10.1021\/op200275d"},{"key":"e_1_2_3_67_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201410744"},{"key":"e_1_2_3_67_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201410744"},{"key":"e_1_2_3_68_1","unstructured":"\u00a0"},{"key":"e_1_2_3_69_2","doi-asserted-by":"publisher","DOI":"10.1021\/op0501500"},{"key":"e_1_2_3_70_2","doi-asserted-by":"publisher","DOI":"10.1002\/tcr.201000020"},{"key":"e_1_2_3_71_2","doi-asserted-by":"publisher","DOI":"10.1038\/ncomms1264"},{"key":"e_1_2_3_72_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201713031"},{"key":"e_1_2_3_72_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201713031"},{"key":"e_1_2_3_73_1","unstructured":"\u00a0"},{"key":"e_1_2_3_74_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0512069"},{"key":"e_1_2_3_75_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6CY00331A"},{"key":"e_1_2_3_76_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201708598"},{"key":"e_1_2_3_76_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201708598"},{"key":"e_1_2_3_77_1","unstructured":"\u00a0"},{"key":"e_1_2_3_78_2","doi-asserted-by":"publisher","DOI":"10.1002\/cctc.201402483"},{"key":"e_1_2_3_79_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5CS00902B"},{"key":"e_1_2_3_80_2","doi-asserted-by":"publisher","DOI":"10.1556\/1846.2016.00014"},{"key":"e_1_2_3_81_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b01590"},{"key":"e_1_2_3_82_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201803961"},{"key":"e_1_2_3_82_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201803961"},{"key":"e_1_2_3_83_2","doi-asserted-by":"publisher","DOI":"10.1038\/nprot.2017.141"},{"key":"e_1_2_3_84_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201903353"},{"key":"e_1_2_3_85_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c01991"},{"key":"e_1_2_3_86_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202012085"},{"key":"e_1_2_3_86_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202012085"},{"key":"e_1_2_3_87_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202103031"},{"key":"e_1_2_3_87_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202103031"},{"key":"e_1_2_3_88_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1SC00685A"},{"key":"e_1_2_3_89_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202203807"},{"key":"e_1_2_3_89_3","doi-asserted-by":"crossref","DOI":"10.1002\/ange.202203807","volume":"134","year":"2022","journal-title":"Angew. Chem."},{"key":"e_1_2_3_90_1","unstructured":"Hexanes was used instead of pentane since the tubing of the peristaltic pumps show reduced lifetime using pentane."},{"key":"e_1_2_3_91_1","unstructured":"\u00a0"},{"key":"e_1_2_3_92_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0108767383001762"},{"key":"e_1_2_3_93_2","doi-asserted-by":"publisher","DOI":"10.3390\/chemistry2030049"},{"key":"e_1_2_3_94_1","unstructured":"Deposition number\u20052210094 (forS-4\u2009d)contains 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_3_95_1","unstructured":"The other diastereosiomer (2\u2032S 3R)-4\u2009l(Scheme\u20052) was also successfully reduced to the corresponding amine (2\u2032S 3R)-8. For details see Supporting Information."},{"key":"e_1_2_3_96_1","doi-asserted-by":"publisher","DOI":"10.1002\/cctc.201900806"},{"key":"e_1_2_3_97_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201300275"},{"key":"e_1_2_3_97_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201300275"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202214377","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202214377","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202214377","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,30]],"date-time":"2023-10-30T09:46:45Z","timestamp":1698659205000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202214377"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,11,29]]},"references-count":119,"journal-issue":{"issue":"1","published-print":{"date-parts":[[2023,1,2]]}},"alternative-id":["10.1002\/anie.202214377"],"URL":"https:\/\/doi.org\/10.1002\/anie.202214377","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,11,29]]},"assertion":[{"value":"2022-09-29","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2022-11-29","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202214377"}}