{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,24]],"date-time":"2026-09-24T11:16:22Z","timestamp":1790248582429,"version":"4.1.0"},"reference-count":73,"publisher":"Wiley","issue":"19","license":[{"start":{"date-parts":[[2018,3,30]],"date-time":"2018-03-30T00:00:00Z","timestamp":1522368000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2018,5,4]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Optically enriched secondary alkyl iodides were converted into secondary alkyllithium and secondary alkylcopper compounds with very high retention of configuration. Quenching with various electrophiles, including chiral epoxides, provided a range of chiral molecules with high enantiomeric purity (&gt;90\u2009%\u2005<jats:italic>ee<\/jats:italic>). This method has been applied in an iterative fashion in the total synthesis of (\u2212)\u2010lardolure in 13 steps and 5.4\u2009% overall yield (&gt;99\u2009%\u2005<jats:italic>ee<\/jats:italic>, dr&gt;99:1) and siphonarienal in 15 steps and 5.6\u2009% overall yield (&gt;99\u2009%\u2005<jats:italic>ee<\/jats:italic>, dr&gt;99:1) starting from commercially available ethyl (<jats:italic>R<\/jats:italic>)\u20103\u2010hydroxybutyrate (&gt;99\u2009%\u2005<jats:italic>ee<\/jats:italic>).<\/jats:p>","DOI":"10.1002\/anie.201800792","type":"journal-article","created":{"date-parts":[[2018,3,7]],"date-time":"2018-03-07T09:38:44Z","timestamp":1520415524000},"page":"5516-5519","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":37,"title":["Preparation of Optically Enriched Secondary Alkyllithium and Alkylcopper Reagents\u2014Synthesis of (\u2212)\u2010Lardolure and Siphonarienal"],"prefix":"10.1002","volume":"57","author":[{"given":"Varvara","family":"Morozova","sequence":"first","affiliation":[{"name":"Department Chemie Ludwig-Maximilians-Universit\u00e4t M\u00fcnchen  Butenandtstrasse 5-13 81377 M\u00fcnchen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Juri","family":"Skotnitzki","sequence":"additional","affiliation":[{"name":"Department Chemie Ludwig-Maximilians-Universit\u00e4t M\u00fcnchen  Butenandtstrasse 5-13 81377 M\u00fcnchen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kohei","family":"Moriya","sequence":"additional","affiliation":[{"name":"Department Chemie Ludwig-Maximilians-Universit\u00e4t M\u00fcnchen  Butenandtstrasse 5-13 81377 M\u00fcnchen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Konstantin","family":"Karaghiosoff","sequence":"additional","affiliation":[{"name":"Department Chemie Ludwig-Maximilians-Universit\u00e4t M\u00fcnchen  Butenandtstrasse 5-13 81377 M\u00fcnchen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5018-8839","authenticated-orcid":false,"given":"Paul","family":"Knochel","sequence":"additional","affiliation":[{"name":"Department Chemie Ludwig-Maximilians-Universit\u00e4t M\u00fcnchen  Butenandtstrasse 5-13 81377 M\u00fcnchen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2018,3,30]]},"reference":[{"key":"e_1_2_2_1_1","unstructured":"\u00a0"},{"key":"e_1_2_2_2_2","volume-title":"Organolithiums: Selectivity for Synthesis","author":"Clayden J.","year":"2002"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1007\/b94542"},{"key":"e_1_2_2_4_2","volume-title":"Classics in Stereoselective Synthesis","author":"Carreira E. 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For new conditions see the Supporting Information."},{"key":"e_1_2_2_57_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201505740"},{"key":"e_1_2_2_57_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201505740"},{"key":"e_1_2_2_58_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201601911"},{"key":"e_1_2_2_59_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0035-1562096"},{"key":"e_1_2_2_60_1","unstructured":"For the synthesis of chiral epoxides see"},{"key":"e_1_2_2_61_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200705326"},{"key":"e_1_2_2_61_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200705326"},{"key":"e_1_2_2_62_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201210198"},{"key":"e_1_2_2_62_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201210198"},{"key":"e_1_2_2_63_1","unstructured":"The crude reaction mixture indicates a slight epimerization at C(2) (crude dr=97:3). After chromatographic purification the dr at C(2) was >99:1."},{"key":"e_1_2_2_64_1","unstructured":"Methylation with (MeO)2SO2proceeds in only 28\u2009% yield (see the Supporting Information)."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201800792","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201800792","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.201800792","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201800792","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2024,6,21]],"date-time":"2024-06-21T15:08:23Z","timestamp":1718982503000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201800792"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,3,30]]},"references-count":73,"journal-issue":{"issue":"19","published-print":{"date-parts":[[2018,5,4]]}},"alternative-id":["10.1002\/anie.201800792"],"URL":"https:\/\/doi.org\/10.1002\/anie.201800792","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,3,30]]},"assertion":[{"value":"2018-01-19","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2018-03-30","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}