{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,5]],"date-time":"2026-10-05T12:52:13Z","timestamp":1791204733991,"version":"4.1.0"},"reference-count":31,"publisher":"Wiley","issue":"2","license":[{"start":{"date-parts":[[2023,11,6]],"date-time":"2023-11-06T00:00:00Z","timestamp":1699228800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc\/4.0\/"},{"start":{"date-parts":[[2023,11,6]],"date-time":"2023-11-06T00:00:00Z","timestamp":1699228800000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2024,1,8]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Vinyl ethers are valuable synthetic intermediates which are also found as natural products, including aflatoxins, rifamycins and plasmalogens. The latter are ubiquitous phospholipids in human cells and contain a vinyl ether moiety with specifically\n                    <jats:italic>Z<\/jats:italic>\n                    configuration. Although numerous methods are available for synthesis of vinyl ethers, there is a lack of methods for obtaining Z isomers of molecules of the type RCH=CHOR\u2019 that are applicable to plasmalogens. A variant of the Peterson reaction is described that generates such molecules with very high stereoselectivity (\n                    <jats:italic>Z<\/jats:italic>\n                    \/\n                    <jats:italic>E<\/jats:italic>\n                    ratio: 99\u2009:\u20091). (\n                    <jats:italic>R,R<\/jats:italic>\n                    )\/(\n                    <jats:italic>S,S<\/jats:italic>\n                    )\u20101\u2010alkoxy\u20102\u2010hydroxyalkylsilanes were synthesized from 1\u2010trimethylsilylalkynes by a sequence of reduction with di\u2010isobutylaluminium hydride to a (\n                    <jats:italic>Z<\/jats:italic>\n                    )\u20101\u2010trimethylsilylalkene, epoxidation of the alkene to a 2\u2010trimethylsilyl\u20103\u2010substituted epoxide and regioselective, boron\u2010trifluoride catalyzed ring\u2010opening of the epoxide by reaction with an alcohol. Conversion of the (\n                    <jats:italic>R,R<\/jats:italic>\n                    )\/(\n                    <jats:italic>S,S<\/jats:italic>\n                    )\u20101\u2010alkoxy\u20102\u2010hydroxyalkylsilanes to vinyl ethers (RCH=CHOR\u2019) was achieved under basic conditions as in a standard Peterson reaction. However, near exclusive formation of a\n                    <jats:italic>Z<\/jats:italic>\n                    vinyl ether was only achieved when the reaction was performed using potassium hydride in the non\u2010polar solvent \u03b1,\u03b1,\u03b1\u2010trifluorotoluene, more polar solvents giving increasing amounts of the\n                    <jats:italic>E<\/jats:italic>\n                    isomer. The sequence described embraces a variety of substituents and precursors, proceeds in overall high yield and is readily scalable.\n                  <\/jats:p>","DOI":"10.1002\/chem.202302708","type":"journal-article","created":{"date-parts":[[2023,9,21]],"date-time":"2023-09-21T06:31:29Z","timestamp":1695277889000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Harnessing the Peterson Reaction for the Stereospecific Synthesis of\n                    <i>Z<\/i>\n                    \u2010Vinyl Ethers"],"prefix":"10.1002","volume":"30","author":[{"given":"Jay","family":"Tromans","sequence":"first","affiliation":[{"name":"School of Natural and Environmental Sciences \u2013 Chemistry Newcastle University Bedson Building Newcastle University  Newcastle upon Tyne NE1 7RU UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bian","family":"Zhang","sequence":"additional","affiliation":[{"name":"BiBerChem Research Ltd. The Biosphere  Draymans Way, Newcastle Helix Newcastle upon Tyne NE4 5BX UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6291-9344","authenticated-orcid":false,"given":"Bernard T.","family":"Golding","sequence":"additional","affiliation":[{"name":"School of Natural and Environmental Sciences \u2013 Chemistry Newcastle University Bedson Building Newcastle University  Newcastle upon Tyne NE1 7RU UK"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2023,11,6]]},"reference":[{"key":"e_1_2_9_1_1","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.18781920108"},{"key":"e_1_2_9_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.196902951"},{"key":"e_1_2_9_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201900478"},{"key":"e_1_2_9_4_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF02537215"},{"key":"e_1_2_9_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00763a047"},{"key":"e_1_2_9_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.0c00851"},{"key":"e_1_2_9_7_1","doi-asserted-by":"publisher","DOI":"10.3390\/foods9050644"},{"key":"e_1_2_9_8_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1NP00067E"},{"key":"e_1_2_9_9_1","volume":"10","author":"Dorninger F.","year":"2022","journal-title":"Cell Dev. 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