{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,1]],"date-time":"2026-10-01T02:34:54Z","timestamp":1790822094640,"version":"4.1.0"},"reference-count":96,"publisher":"Wiley","issue":"33","license":[{"start":{"date-parts":[[2024,7,16]],"date-time":"2024-07-16T00:00:00Z","timestamp":1721088000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["22171231"],"award-info":[{"award-number":["22171231"]}],"id":[{"id":"10.13039\/501100001809","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":[[2024,8,12]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>This study describes an unprecedented chromium\u2010catalyzed asymmetric Reformatsky reaction, enabling the synthesis of chiral <jats:italic>\u03b2<\/jats:italic>\u2010hydroxy carbonyl compounds from <jats:italic>\u03b1<\/jats:italic>\u2010chlorinated or <jats:italic>\u03b1<\/jats:italic>\u2010brominated esters and amides. By employing a chiral chromium\/diarylamine bis(oxazoline) catalyst, we achieved relatively broad functional group tolerance. Distinct from known reports, the protocol operates under both classical and photoredox conditions, facilitated by the in situ formation of a nucleophilic chiral chromium intermediate through a radical\u2010polar crossover mechanism. Preliminary mechanistic insights, supported by DFT calculations, identify the nucleophilic aldehyde addition as the key stereo\u2010determining step. This approach not only overcomes the limitations of existing Reformatsky reactions but also provides a versatile strategy for accessing complex chiral molecules.<\/jats:p>","DOI":"10.1002\/anie.202406109","type":"journal-article","created":{"date-parts":[[2024,6,5]],"date-time":"2024-06-05T12:28:16Z","timestamp":1717590496000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":36,"title":["Chromium Catalyzed Asymmetric Reformatsky Reaction"],"prefix":"10.1002","volume":"63","author":[{"given":"Yong\u2010Feng","family":"Lv","sequence":"first","affiliation":[{"name":"Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry, School of Science and Research Center for Industries of the Future Westlake University  Hangzhou 310030, Zhejiang Province China"},{"name":"Institute of Natural Sciences Westlake Institute for Advanced Study  Hangzhou 310024, Zhejiang Province China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gang","family":"Liu","sequence":"additional","affiliation":[{"name":"Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry, School of Science and Research Center for Industries of the Future Westlake University  Hangzhou 310030, Zhejiang Province China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhaoxin","family":"Shi","sequence":"additional","affiliation":[{"name":"Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry, School of Science and Research Center for Industries of the Future Westlake University  Hangzhou 310030, Zhejiang Province China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7934-2879","authenticated-orcid":false,"given":"Zhaobin","family":"Wang","sequence":"additional","affiliation":[{"name":"Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry, School of Science and Research Center for Industries of the Future Westlake University  Hangzhou 310030, Zhejiang Province China"},{"name":"Institute of Natural Sciences Westlake Institute for Advanced Study  Hangzhou 310024, Zhejiang Province China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,7,16]]},"reference":[{"key":"e_1_2_8_1_1","unstructured":"\u00a0"},{"key":"e_1_2_8_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr000411y"},{"key":"e_1_2_8_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar970347f"},{"key":"e_1_2_8_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr078340r"},{"key":"e_1_2_8_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201801023"},{"key":"e_1_2_8_6_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.aah5133"},{"key":"e_1_2_8_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.0c00053"},{"key":"e_1_2_8_8_1","unstructured":"\u00a0"},{"key":"e_1_2_8_9_2","doi-asserted-by":"publisher","DOI":"10.1039\/C2CS35351B"},{"key":"e_1_2_8_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200604344"},{"key":"e_1_2_8_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201300571"},{"key":"e_1_2_8_12_2","doi-asserted-by":"publisher","DOI":"10.3762\/bjoc.14.21"},{"key":"e_1_2_8_13_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2004.07.018"},{"key":"e_1_2_8_14_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1989-27326"},{"key":"e_1_2_8_15_1","unstructured":"\u00a0"},{"key":"e_1_2_8_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja001460v"},{"key":"e_1_2_8_17_2","doi-asserted-by":"publisher","DOI":"10.1039\/b104949f"},{"key":"e_1_2_8_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja027675h"},{"key":"e_1_2_8_19_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2008.01.116"},{"key":"e_1_2_8_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201901069"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1351\/pac200880050891"},{"key":"e_1_2_8_22_1","unstructured":"\u00a0"},{"key":"e_1_2_8_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo9914317"},{"key":"e_1_2_8_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo030082k"},{"key":"e_1_2_8_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200462757"},{"key":"e_1_2_8_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0531381"},{"key":"e_1_2_8_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0531435"},{"key":"e_1_2_8_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol500631j"},{"key":"e_1_2_8_29_1","unstructured":"\u00a0"},{"key":"e_1_2_8_30_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200504239"},{"key":"e_1_2_8_31_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200606178"},{"key":"e_1_2_8_32_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200704841"},{"key":"e_1_2_8_33_2","doi-asserted-by":"publisher","DOI":"10.1039\/b805197f"},{"key":"e_1_2_8_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol801574m"},{"key":"e_1_2_8_35_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.2008.1298"},{"key":"e_1_2_8_36_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201604606"},{"key":"e_1_2_8_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b03669"},{"key":"e_1_2_8_38_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.202000768"},{"key":"e_1_2_8_39_1","unstructured":"\u00a0"},{"key":"e_1_2_8_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00451a061"},{"key":"e_1_2_8_41_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)82859-8"},{"key":"e_1_2_8_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00278a057"},{"key":"e_1_2_8_43_1","unstructured":"\u00a0"},{"key":"e_1_2_8_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr9703360"},{"key":"e_1_2_8_45_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200700324"},{"key":"e_1_2_8_46_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0036-1589457"},{"key":"e_1_2_8_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.7b00144"},{"key":"e_1_2_8_48_2","first-page":"1684","volume":"54","author":"Kanai M.","year":"2021","journal-title":"Synthesis"},{"key":"e_1_2_8_49_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.1c00799"},{"key":"e_1_2_8_50_1","doi-asserted-by":"publisher","DOI":"10.1016\/B978-0-08-097742-3.00108-7"},{"key":"e_1_2_8_51_1","unstructured":"\u00a0"},{"key":"e_1_2_8_52_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-022-32614-4"},{"key":"e_1_2_8_53_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c12043"},{"key":"e_1_2_8_54_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.chempr.2024.01.003"},{"key":"e_1_2_8_55_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202117114"},{"key":"e_1_2_8_56_1","unstructured":"\u00a0"},{"key":"e_1_2_8_57_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9625236"},{"key":"e_1_2_8_58_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(19991115)38:22<3357::AID-ANIE3357>3.0.CO;2-W"},{"key":"e_1_2_8_59_1","unstructured":"\u00a0"},{"key":"e_1_2_8_60_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol047661b"},{"key":"e_1_2_8_61_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja905843e"},{"key":"e_1_2_8_62_1","unstructured":"\u00a0"},{"key":"e_1_2_8_63_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2006.11.055"},{"key":"e_1_2_8_64_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201003366"},{"key":"e_1_2_8_65_1","unstructured":"\u00a0"},{"key":"e_1_2_8_66_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr500277b"},{"key":"e_1_2_8_67_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.1c00632"},{"key":"e_1_2_8_68_1","unstructured":"\u00a0"},{"key":"e_1_2_8_69_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.1c00383"},{"key":"e_1_2_8_70_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.1c00403"},{"key":"e_1_2_8_71_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1CS00210D"},{"key":"e_1_2_8_72_2","doi-asserted-by":"publisher","DOI":"10.1007\/s11426-019-9701-5"},{"key":"e_1_2_8_73_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2019.213129"},{"key":"e_1_2_8_74_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr300503r"},{"key":"e_1_2_8_75_2","doi-asserted-by":"publisher","DOI":"10.1039\/D3CC04671K"},{"key":"e_1_2_8_76_1","unstructured":"\u00a0"},{"key":"e_1_2_8_77_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja905491p"},{"key":"e_1_2_8_78_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2009.09.107"},{"key":"e_1_2_8_79_1","unstructured":"\u00a0"},{"key":"e_1_2_8_80_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2004.04.056"},{"key":"e_1_2_8_81_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2016.02.022"},{"key":"e_1_2_8_82_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200700184"},{"key":"e_1_2_8_83_2","doi-asserted-by":"publisher","DOI":"10.1039\/B705665F"},{"key":"e_1_2_8_84_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00100a004"},{"key":"e_1_2_8_85_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja1083392"},{"key":"e_1_2_8_86_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja01565a041"},{"key":"e_1_2_8_87_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-019-0319-5"},{"key":"e_1_2_8_88_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c03007"},{"key":"e_1_2_8_89_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja052071"},{"key":"e_1_2_8_90_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00214-007-0310-x"},{"key":"e_1_2_8_91_1","doi-asserted-by":"publisher","DOI":"10.1039\/b508541a"},{"key":"e_1_2_8_92_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF01114537"},{"key":"e_1_2_8_93_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp810292n"},{"key":"e_1_2_8_94_1","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.22885"},{"key":"e_1_2_8_95_1","unstructured":"L.\u2005C. CYLview 1.0 B. Universit\u00e9 De Sherbrooke2009."},{"key":"e_1_2_8_96_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-019-0319-5"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202406109","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,3,12]],"date-time":"2025-03-12T06:55:10Z","timestamp":1741762510000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202406109"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,7,16]]},"references-count":96,"journal-issue":{"issue":"33","published-print":{"date-parts":[[2024,8,12]]}},"alternative-id":["10.1002\/anie.202406109"],"URL":"https:\/\/doi.org\/10.1002\/anie.202406109","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,7,16]]},"assertion":[{"value":"2024-03-30","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2024-07-16","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202406109"}}