{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,23]],"date-time":"2026-02-23T00:36:40Z","timestamp":1771807000611,"version":"3.50.1"},"reference-count":81,"publisher":"Wiley","issue":"24","license":[{"start":{"date-parts":[[2021,10,22]],"date-time":"2021-10-22T00:00:00Z","timestamp":1634860800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["aces.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry \u0097 An Asian Journal"],"published-print":{"date-parts":[[2021,12,13]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>This study reports the first base\u2010promoted aldol\u2013Tishchenko reactions of allylic alcohols with aldehydes initiated by allylic isomerization. The reaction enables the diastereoselective synthesis of a variety of 1,3\u2010diols with three contiguous stereogenic centers. Unlike commonly reported systems, our method allows the use of readily available allylic alcohols as nucleophiles instead of enolizable aldehydes and ketones.<\/jats:p>","DOI":"10.1002\/asia.202101093","type":"journal-article","created":{"date-parts":[[2021,10,15]],"date-time":"2021-10-15T13:20:18Z","timestamp":1634304018000},"page":"4053-4056","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Potassium Base\u2010Promoted Diastereoselective Synthesis of 1,3\u2010Diols from Allylic Alcohols and Aldehydes through a Tandem Allylic\u2010Isomerization\/Aldol\u2013Tishchenko Reaction"],"prefix":"10.1002","volume":"16","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-5018-917X","authenticated-orcid":false,"given":"Masahiro","family":"Sai","sequence":"first","affiliation":[{"name":"Department of Chemistry and Biomolecular Science Faculty of Engineering Gifu University  1-1 Yanagido Gifu 501-1193 Japan"},{"name":"Research Foundation ITSUU Laboratory C1232 Kanagawa Science Park R &amp; D Building  3-2-1 Sakado Takatsu-ku Kawasaki Kanagawa 213-0012 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2021,10,22]]},"reference":[{"key":"e_1_2_2_1_1","unstructured":"\u00a0"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00038a011"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20000818)39:16<2847::AID-ANIE2847>3.0.CO;2-0"},{"key":"e_1_2_2_3_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20000818)112:16<2967::AID-ANGE2967>3.0.CO;2-H"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/np070558l"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr900019j"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/np100918z"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2012.03.077"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja404401f"},{"key":"e_1_2_2_9_1","unstructured":"\u00a0"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1990-26966"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(19980605)37:10<1375::AID-ANIE1375>3.0.CO;2-H"},{"key":"e_1_2_2_11_3","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3757(19980518)110:10<1445::AID-ANGE1445>3.0.CO;2-R"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2006-926315"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3cy00125c"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6OB01925K"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9OB02675D"},{"key":"e_1_2_2_16_1","unstructured":"For reviews see:"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.2174\/1385272033486224"},{"key":"e_1_2_2_18_2","doi-asserted-by":"crossref","first-page":"327","DOI":"10.1002\/9783527619566.ch15","volume-title":"Modern Aldol Reactions, Vol. 2","author":"Mahrwald R.","year":"2004"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200600258"},{"key":"e_1_2_2_20_2","first-page":"2310","volume":"2012","author":"Ralston K. 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Soc. Chim. 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The reaction using pivalaldehyde led to no formation of addition products due to the poor reactivity."},{"key":"e_1_2_2_75_1","unstructured":"Ketones generated by allylic isomerization of1were often detected by1H NMR analysis of the crude reaction mixture."},{"key":"e_1_2_2_76_1","unstructured":"The stereochemistry of21was unambiguously identified by spectroscopic and X-ray crystallographic analysis and all of 1 3-diol products were assigned by analogy. CCDC 1972662 contains the supplementary crystallographic data for21. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk\/data\u2002request\/cif."},{"key":"e_1_2_2_77_1","unstructured":"When (E)-3-phenyl-1-(o-tolyl)prop-2-en-1-ol was employed the allylic isomerization did not proceed."},{"key":"e_1_2_2_78_1","unstructured":"The first step of allylic isomerization is a rate-determining 1 2-hydride shift which produces a negative charge at the C3 position. 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