{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T18:07:44Z","timestamp":1790705264064,"version":"4.1.0"},"reference-count":149,"publisher":"Wiley","issue":"39","license":[{"start":{"date-parts":[[2018,7,26]],"date-time":"2018-07-26T00:00:00Z","timestamp":1532563200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100014364","name":"Samsung Science and Technology Foundation","doi-asserted-by":"crossref","award":["SSTF-BA1701-11"],"award-info":[{"award-number":["SSTF-BA1701-11"]}],"id":[{"id":"10.13039\/501100014364","id-type":"DOI","asserted-by":"crossref"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2018,9,24]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>We report the successful generation of (diborylmethyl)zinc(II) species by transmetallation beteween isolable (diborylmethyl)lithium and zinc(II) halide (X=Br, Cl) and their application in the synthesis of enantioenriched <jats:italic>gem<\/jats:italic>\u2010diborylalkanes bearing a stereogenic center at the \u03b2\u2010position of the diboryl groups by an asymmetric allylic substitution reaction. The reaction has a broad substrate scope, and various enantioenriched <jats:italic>gem<\/jats:italic>\u2010diborylalkanes can be obtained in good yields with excellent enantioselectivity. Further elaboration of the enantioenriched <jats:italic>gem<\/jats:italic>\u2010diborylalkanes provides access to a diverse set of valuable chiral building blocks.<\/jats:p>","DOI":"10.1002\/anie.201805476","type":"journal-article","created":{"date-parts":[[2018,7,2]],"date-time":"2018-07-02T14:46:25Z","timestamp":1530542785000},"page":"12930-12934","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":111,"title":["Generation and Application of (Diborylmethyl)zinc(II) Species: Access to Enantioenriched <i>gem<\/i>\u2010Diborylalkanes by an Asymmetric Allylic Substitution"],"prefix":"10.1002","volume":"57","author":[{"given":"Yeosan","family":"Lee","sequence":"first","affiliation":[{"name":"Department of Chemistry Pohang University of Science and Technology (POSTECH)  Pohang 37673 Rep. of Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jinyoung","family":"Park","sequence":"additional","affiliation":[{"name":"Department of Chemistry Pohang University of Science and Technology (POSTECH)  Pohang 37673 Rep. of Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5803-4922","authenticated-orcid":false,"given":"Seung Hwan","family":"Cho","sequence":"additional","affiliation":[{"name":"Department of Chemistry Pohang University of Science and Technology (POSTECH)  Pohang 37673 Rep. of Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2018,7,26]]},"reference":[{"key":"e_1_2_2_1_1","unstructured":"\u00a0"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7CC01254C"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00162"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5CS00338E"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b08326"},{"key":"e_1_2_2_6_1","unstructured":"\u00a0"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/om011012b"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0028-1088131"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1039\/C3SC52824C"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201402458"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol403338s"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5b01135"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b12249"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7GC01161J"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-017-00363-4"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b02518"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7OB00654C"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201710389"},{"key":"e_1_2_2_18_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201710389"},{"key":"e_1_2_2_19_1","unstructured":"\u00a0"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201701390"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7OB02978K"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2018.04.061"},{"key":"e_1_2_2_23_1","unstructured":"Examples for catalytic non-enantioselective reactions see:"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja105176v"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201407000"},{"key":"e_1_2_2_25_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201407000"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201507171"},{"key":"e_1_2_2_26_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201507171"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6RA09959A"},{"key":"e_1_2_2_28_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5CC09817C"},{"key":"e_1_2_2_29_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201509840"},{"key":"e_1_2_2_29_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201509840"},{"key":"e_1_2_2_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5b03692"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7CC00129K"},{"key":"e_1_2_2_32_1","unstructured":"Examples for catalytic enantioselective reactions see:"},{"key":"e_1_2_2_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja510266x"},{"key":"e_1_2_2_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja500029w"},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b03477"},{"key":"e_1_2_2_36_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201603465"},{"key":"e_1_2_2_36_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201603465"},{"key":"e_1_2_2_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6b00376"},{"key":"e_1_2_2_38_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201600309"},{"key":"e_1_2_2_38_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201600309"},{"key":"e_1_2_2_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.6b00719"},{"key":"e_1_2_2_40_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201705829"},{"key":"e_1_2_2_40_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201705829"},{"key":"e_1_2_2_41_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201702611"},{"key":"e_1_2_2_41_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201702611"},{"key":"e_1_2_2_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b06408"},{"key":"e_1_2_2_43_1","unstructured":"\u00a0"},{"key":"e_1_2_2_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja505455z"},{"key":"e_1_2_2_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja510081r"},{"key":"e_1_2_2_46_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201603329"},{"key":"e_1_2_2_46_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201603329"},{"key":"e_1_2_2_47_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0036-1588073"},{"key":"e_1_2_2_48_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6SC05338F"},{"key":"e_1_2_2_49_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7CC03731G"},{"key":"e_1_2_2_50_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b11757"},{"key":"e_1_2_2_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b01821"},{"key":"e_1_2_2_52_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201712351"},{"key":"e_1_2_2_52_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201712351"},{"key":"e_1_2_2_53_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201801679"},{"key":"e_1_2_2_53_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201801679"},{"key":"e_1_2_2_54_1","unstructured":"\u00a0"},{"key":"e_1_2_2_55_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-328X(00)90155-4"},{"key":"e_1_2_2_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00451a071"},{"key":"e_1_2_2_57_2","doi-asserted-by":"publisher","DOI":"10.1021\/om00061a005"},{"key":"e_1_2_2_58_1","unstructured":"\u00a0"},{"key":"e_1_2_2_59_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5b00480"},{"key":"e_1_2_2_60_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b01474"},{"key":"e_1_2_2_61_1","unstructured":"\u00a0"},{"key":"e_1_2_2_62_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b09309"},{"key":"e_1_2_2_63_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b03853"},{"key":"e_1_2_2_64_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b12941"},{"key":"e_1_2_2_65_1","unstructured":"\u00a0"},{"key":"e_1_2_2_66_2","first-page":"3833","author":"Miguel Y.","year":"2004","journal-title":"Eur. J. Org. Chem."},{"key":"e_1_2_2_67_2","volume-title":"The Chemistry of Organozinc Compounds","year":"2006"},{"key":"e_1_2_2_68_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00022a008"},{"key":"e_1_2_2_69_2","doi-asserted-by":"publisher","DOI":"10.1021\/om200637s"},{"key":"e_1_2_2_70_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1ob06372c"},{"key":"e_1_2_2_71_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja4054114"},{"key":"e_1_2_2_72_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo500297r"},{"key":"e_1_2_2_73_1","unstructured":"For representative reviews see:"},{"key":"e_1_2_2_74_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr9409804"},{"key":"e_1_2_2_75_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr020027w"},{"key":"e_1_2_2_76_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar020153m"},{"key":"e_1_2_2_77_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200605113"},{"key":"e_1_2_2_77_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200605113"},{"key":"e_1_2_2_78_1","unstructured":"For selected reviews see:"},{"key":"e_1_2_2_79_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0683515"},{"key":"e_1_2_2_80_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr068424k"},{"key":"e_1_2_2_81_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200904948"},{"key":"e_1_2_2_81_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200904948"},{"key":"e_1_2_2_82_1","unstructured":"For reviews of iridium-catalyzed allylic substitutions see:"},{"key":"e_1_2_2_83_2","first-page":"1641","author":"Miyabe H.","year":"2005","journal-title":"Synlett"},{"key":"e_1_2_2_84_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2006-950284"},{"key":"e_1_2_2_85_2","doi-asserted-by":"publisher","DOI":"10.1039\/B614169B"},{"key":"e_1_2_2_86_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar100047x"},{"key":"e_1_2_2_87_2","doi-asserted-by":"publisher","DOI":"10.1007\/978-3-642-15334-1_7"},{"key":"e_1_2_2_88_2","doi-asserted-by":"publisher","DOI":"10.1007\/3418_2011_10"},{"key":"e_1_2_2_89_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2ob07086c"},{"key":"e_1_2_2_90_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.6b01886"},{"key":"e_1_2_2_91_1","unstructured":"\u00a0"},{"key":"e_1_2_2_92_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0112036"},{"key":"e_1_2_2_93_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja028614m"},{"key":"e_1_2_2_94_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201108287"},{"key":"e_1_2_2_94_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201108287"},{"key":"e_1_2_2_95_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5b00058"},{"key":"e_1_2_2_96_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.organomet.6b00339"},{"key":"e_1_2_2_97_1","unstructured":"The purity of2\u2009awas determined by titration using diphenylacetic acid as a titrant. For details see the Supporting Information."},{"key":"e_1_2_2_98_1","unstructured":"See the Supporting Information for details."},{"key":"e_1_2_2_99_1","unstructured":"For a recent review see:"},{"key":"e_1_2_2_100_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.7b00300"},{"key":"e_1_2_2_101_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b12421"},{"key":"e_1_2_2_102_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b02856"},{"key":"e_1_2_2_103_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201706374"},{"key":"e_1_2_2_103_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201706374"},{"key":"e_1_2_2_104_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b01346"},{"key":"e_1_2_2_105_1","unstructured":"We assumed that the coordination of zinc to one of oxygens of Bpin group might have an effect to stabilize (diborylmethyl)zinc species. For details see:"},{"key":"e_1_2_2_106_2","doi-asserted-by":"publisher","DOI":"10.1021\/om50003a004"},{"key":"e_1_2_2_107_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00345a074"},{"key":"e_1_2_2_108_2","doi-asserted-by":"publisher","DOI":"10.1021\/om00082a019"},{"key":"e_1_2_2_109_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00264a039"},{"key":"e_1_2_2_110_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo972041s"},{"key":"e_1_2_2_111_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo4013942"},{"key":"e_1_2_2_112_1","unstructured":"\u00a0"},{"key":"e_1_2_2_113_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(19990201)38:3<379::AID-ANIE379>3.0.CO;2-Y"},{"key":"e_1_2_2_113_3","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3757(19990201)111:3<391::AID-ANGE391>3.0.CO;2-M"},{"key":"e_1_2_2_114_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20010417)40:8<1456::AID-ANIE1456>3.0.CO;2-T"},{"key":"e_1_2_2_114_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20010417)113:8<1504::AID-ANGE1504>3.0.CO;2-V"},{"key":"e_1_2_2_115_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0156289"},{"key":"e_1_2_2_116_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0300618"},{"key":"e_1_2_2_117_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200390088"},{"key":"e_1_2_2_117_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200390056"},{"key":"e_1_2_2_118_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja046245j"},{"key":"e_1_2_2_119_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200303207"},{"key":"e_1_2_2_120_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200463028"},{"key":"e_1_2_2_120_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200463028"},{"key":"e_1_2_2_121_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200900054"},{"key":"e_1_2_2_122_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201309074"},{"key":"e_1_2_2_122_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201309074"},{"key":"e_1_2_2_123_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4CS00430B"},{"key":"e_1_2_2_124_1","unstructured":"\u00a0"},{"key":"e_1_2_2_125_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200801879"},{"key":"e_1_2_2_126_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201501851"},{"key":"e_1_2_2_126_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201501851"},{"key":"e_1_2_2_127_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201700433"},{"key":"e_1_2_2_127_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201700433"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201805476","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201805476","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,9,14]],"date-time":"2023-09-14T16:42:58Z","timestamp":1694709778000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201805476"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,7,26]]},"references-count":149,"journal-issue":{"issue":"39","published-print":{"date-parts":[[2018,9,24]]}},"alternative-id":["10.1002\/anie.201805476"],"URL":"https:\/\/doi.org\/10.1002\/anie.201805476","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,7,26]]},"assertion":[{"value":"2018-05-11","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2018-07-26","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}