{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,12]],"date-time":"2026-09-12T15:27:23Z","timestamp":1789226843395,"version":"build-2803163510"},"reference-count":121,"publisher":"Wiley","issue":"38","license":[{"start":{"date-parts":[[2018,6,12]],"date-time":"2018-06-12T00:00:00Z","timestamp":1528761600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100004189","name":"Max-Planck-Gesellschaft","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100004189","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100005156","name":"Alexander von Humboldt-Stiftung","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100005156","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2018,7,5]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Propargyl alcohols are privileged substrates for stereochemically unorthodox\n                    <jats:italic>trans<\/jats:italic>\n                    \u2010hydrostannation reactions catalyzed by [Cp*RuCl]\n                    <jats:sub>4<\/jats:sub>\n                    (Cp*=pentamethylcyclopentadienyl), because an incipient hydrogen bond between the \u2010OH group and the polarized [Ru\u2010Cl] unit assists substrate binding. For this very reason, it is also possible to subject diyne derivatives carrying one \u2010OH group to site\u2010selective stannylation, even if the acetylene units are conjugated and hence, electronically coupled. An unusual temperature dependence was observed in that heating tends to improve site\u2010selectivity, whereas per\u2010stannylation is favored when the reaction is carried out in the cold. This counterintuitive trend can be rationalized based on spectroscopic data; additional support comes from the isolation of the unusual bimetallic complex\n                    <jats:bold>11<\/jats:bold>\n                    . The bridging fulvene and enynyl ligands in\n                    <jats:bold>11<\/jats:bold>\n                    are thought to reflect an interligand redox isomerization process likely triggered by synchronous activation of the 1,3\u2010diyne substrate by two metal centers. The preparative relevance of site\u2010selective\n                    <jats:italic>trans<\/jats:italic>\n                    \u2010hydrostannation is illustrated by the total synthesis of two members of the typhonoside series of glycolipids, which are endowed with neuroprotective properties. Moreover, the preparation of a fluoroalkene sphingosine analogue shows that the tin residue also serves as a versatile handle for late\u2010stage modification of a bioactive target compound.\n                  <\/jats:p>","DOI":"10.1002\/chem.201801344","type":"journal-article","created":{"date-parts":[[2018,4,20]],"date-time":"2018-04-20T10:02:21Z","timestamp":1524218541000},"page":"9667-9674","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":42,"title":["Site\u2010Selective\n                    <i>trans<\/i>\n                    \u2010Hydrostannation of 1,3\u2010 and 1,\n                    <i>n<\/i>\n                    \u2010Diynes: Application to the Total Synthesis of Typhonosides\u2005E and F, and a Fluorinated Cerebroside Analogue"],"prefix":"10.1002","volume":"24","author":[{"given":"Xiaobin","family":"Mo","sequence":"first","affiliation":[{"name":"Max-Planck-Institut f\u00fcr Kohlenforschung  45470 M\u00fclheim\/Ruhr Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Aur\u00e9lien","family":"Letort","sequence":"additional","affiliation":[{"name":"Max-Planck-Institut f\u00fcr Kohlenforschung  45470 M\u00fclheim\/Ruhr Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Drago\u015f\u2010Adrian","family":"Ro\u015fca","sequence":"additional","affiliation":[{"name":"Max-Planck-Institut f\u00fcr Kohlenforschung  45470 M\u00fclheim\/Ruhr Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kosuke","family":"Higashida","sequence":"additional","affiliation":[{"name":"Max-Planck-Institut f\u00fcr Kohlenforschung  45470 M\u00fclheim\/Ruhr Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0098-3417","authenticated-orcid":false,"given":"Alois","family":"F\u00fcrstner","sequence":"additional","affiliation":[{"name":"Max-Planck-Institut f\u00fcr Kohlenforschung  45470 M\u00fclheim\/Ruhr Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2018,6,12]]},"reference":[{"key":"e_1_2_7_1_1","unstructured":"The expressiontrans-hydrogenation (boration silylation germylation stannation) of an alkyne as used herein denotes a reaction in which the H and the E-unit (E=H BR2 SiR3 GeR3 SnR3) end uptransto each other. For the formalism of nomenclature however the resulting products are correctly termedZ-configured for E=SiR3 GeR3 SnR3butE-configured for E=H BR2."},{"key":"e_1_2_7_2_1","unstructured":"\u00a0"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201205946"},{"key":"e_1_2_7_3_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201205946"},{"key":"e_1_2_7_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201506075"},{"key":"e_1_2_7_4_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201506075"},{"key":"e_1_2_7_5_1","unstructured":"\u00a0"},{"key":"e_1_2_7_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0121033"},{"key":"e_1_2_7_7_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2005-861874"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201307584"},{"key":"e_1_2_7_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201307584"},{"key":"e_1_2_7_9_1","unstructured":"\u00a0"},{"key":"e_1_2_7_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201311080"},{"key":"e_1_2_7_10_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201311080"},{"key":"e_1_2_7_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201402719"},{"key":"e_1_2_7_11_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201402719"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b01475"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b12517"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b00665"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.20150317"},{"key":"e_1_2_7_16_1","unstructured":"See also:"},{"key":"e_1_2_7_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201700342"},{"key":"e_1_2_7_17_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201700342"},{"key":"e_1_2_7_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/om0342006"},{"key":"e_1_2_7_19_1","unstructured":"\u00a0"},{"key":"e_1_2_7_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201501608"},{"key":"e_1_2_7_20_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201501608"},{"key":"e_1_2_7_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201701391"},{"key":"e_1_2_7_21_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201701391"},{"key":"e_1_2_7_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6b01431"},{"key":"e_1_2_7_23_2","first-page":"202","author":"Schaubach S.","year":"2017","journal-title":"Synthesis"},{"key":"e_1_2_7_24_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201705550"},{"key":"e_1_2_7_25_2","author":"Meng Z.","year":"2018","journal-title":"J. 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Whereas this pattern is counterintuitive on steric grounds it is in agreement with our mechanistic proposal (see Ref.\u2005[7]) that hydride transfer precedes stannyl transfer: the group which is delivered first is free to take the more accessible position."},{"key":"e_1_2_7_41_1","unstructured":"\u00a0"},{"key":"e_1_2_7_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00142a036"},{"key":"e_1_2_7_43_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja804105m"},{"key":"e_1_2_7_44_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201601163"},{"key":"e_1_2_7_45_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jnatprod.6b00954"},{"key":"e_1_2_7_46_1","unstructured":"See also:"},{"key":"e_1_2_7_47_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(02)00583-X"},{"key":"e_1_2_7_48_2","doi-asserted-by":"publisher","DOI":"10.1080\/10286020108040367"},{"key":"e_1_2_7_49_2","doi-asserted-by":"publisher","DOI":"10.1021\/np960201"},{"key":"e_1_2_7_50_2","doi-asserted-by":"publisher","DOI":"10.1021\/np960670b"},{"key":"e_1_2_7_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/jf302085u"},{"key":"e_1_2_7_52_1","doi-asserted-by":"publisher","DOI":"10.3109\/09687688.2010.538731"},{"key":"e_1_2_7_53_1","unstructured":"For the use of C-silyl substituents as protecting and directing groups see:"},{"key":"e_1_2_7_54_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja2031085"},{"key":"e_1_2_7_55_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja068901g"},{"key":"e_1_2_7_56_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200901449"},{"key":"e_1_2_7_57_2","first-page":"565","author":"Bressy C.","year":"2009","journal-title":"Synlett"},{"key":"e_1_2_7_58_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol070608d"},{"key":"e_1_2_7_59_1","unstructured":"\u00a0"},{"key":"e_1_2_7_60_2","doi-asserted-by":"publisher","DOI":"10.1039\/b307243f"},{"key":"e_1_2_7_61_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2005.02.075"},{"key":"e_1_2_7_62_1","unstructured":"\u00a0"},{"key":"e_1_2_7_63_2","doi-asserted-by":"publisher","DOI":"10.3987\/REV-10-689"},{"key":"e_1_2_7_64_2","doi-asserted-by":"publisher","DOI":"10.1039\/a900943d"},{"key":"e_1_2_7_65_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1998-4494"},{"key":"e_1_2_7_66_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200200518"},{"key":"e_1_2_7_67_1","unstructured":"\u00a0"},{"key":"e_1_2_7_68_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(19990601)38:11<1532::AID-ANIE1532>3.0.CO;2-U"},{"key":"e_1_2_7_68_3","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3757(19990601)111:11<1632::AID-ANGE1632>3.0.CO;2-A"},{"key":"e_1_2_7_69_2","doi-asserted-by":"publisher","DOI":"10.1038\/nrm2329"},{"key":"e_1_2_7_70_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1469-8137.2004.00992.x"},{"key":"e_1_2_7_71_1","unstructured":"For studies into various types of glycolipids from this laboratory see Ref.\u2005[28b \u2009c] and the following:"},{"key":"e_1_2_7_72_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200300728"},{"key":"e_1_2_7_73_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo971918k"},{"key":"e_1_2_7_74_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo9800098"},{"key":"e_1_2_7_75_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja991361l"},{"key":"e_1_2_7_76_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo0012952"},{"key":"e_1_2_7_77_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20020617)41:12<2097::AID-ANIE2097>3.0.CO;2-T"},{"key":"e_1_2_7_77_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20020617)114:12<2203::AID-ANGE2203>3.0.CO;2-M"},{"key":"e_1_2_7_78_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja036521e"},{"key":"e_1_2_7_79_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200305588"},{"key":"e_1_2_7_80_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)01131-5"},{"key":"e_1_2_7_81_1","first-page":"297","volume":"39","author":"Tidwell T. T.","year":"1990","journal-title":"Org. 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These data are provided free of charge byThe Cambridge Crystallographic Data Centre."}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.201801344","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201801344","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T11:23:54Z","timestamp":1760268234000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.201801344"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,6,12]]},"references-count":121,"journal-issue":{"issue":"38","published-print":{"date-parts":[[2018,7,5]]}},"alternative-id":["10.1002\/chem.201801344"],"URL":"https:\/\/doi.org\/10.1002\/chem.201801344","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,6,12]]},"assertion":[{"value":"2018-03-16","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2018-06-12","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}