{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T15:09:03Z","timestamp":1787065743240,"version":"build-2736575974"},"reference-count":28,"publisher":"MDPI AG","issue":"17","license":[{"start":{"date-parts":[[2020,8,27]],"date-time":"2020-08-27T00:00:00Z","timestamp":1598486400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["18H01974"],"award-info":[{"award-number":["18H01974"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Chiral tertiary \u03b1-hydroxyketones were synthesized with high enantiopurity by asymmetric decarboxylative chlorination and subsequent nucleophilic substitution. We recently reported the asymmetric decarboxylative chlorination of \u03b2-ketocarboxylic acids in the presence of a chiral primary amine catalyst to obtain \u03b1-chloroketones with high enantiopurity. Here, we found that nucleophilic substitution of the resulting \u03b1-chloroketones with tetrabutylammonium hydroxide yielded the corresponding \u03b1-hydroxyketones without loss of enantiopurity. The reaction proceeded smoothly even at a tertiary carbon. The proposed method would be useful for the preparation of chiral tertiary alcohols.<\/jats:p>","DOI":"10.3390\/molecules25173902","type":"journal-article","created":{"date-parts":[[2020,8,27]],"date-time":"2020-08-27T09:47:02Z","timestamp":1598521622000},"page":"3902","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["Asymmetric Synthesis of Tertiary \u03b1 -Hydroxyketones by Enantioselective Decarboxylative Chlorination and Subsequent Nucleophilic Substitution"],"prefix":"10.3390","volume":"25","author":[{"given":"Mei Kee","family":"Kam","sequence":"first","affiliation":[{"name":"Department of Applied Chemistry and Life Science, Toyohashi University of Technology, 1-1 Hibarigaoka, Tempaku-cho, Toyohashi 441-8580, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Akira","family":"Sugiyama","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry and Life Science, Toyohashi University of Technology, 1-1 Hibarigaoka, Tempaku-cho, Toyohashi 441-8580, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ryouta","family":"Kawanishi","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry and Life Science, Toyohashi University of Technology, 1-1 Hibarigaoka, Tempaku-cho, Toyohashi 441-8580, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6368-4823","authenticated-orcid":false,"given":"Kazutaka","family":"Shibatomi","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry and Life Science, Toyohashi University of Technology, 1-1 Hibarigaoka, Tempaku-cho, Toyohashi 441-8580, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2020,8,27]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"876","DOI":"10.1002\/adsc.201801023","article-title":"Recent advances in catalytic asymmetric synthesis of tertiary alcohols via nucleophilic addition to ketones","volume":"361","author":"Liu","year":"2019","journal-title":"Adv. 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