{"id":190,"date":"2021-11-24T21:50:27","date_gmt":"2021-11-24T12:50:27","guid":{"rendered":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/?p=190"},"modified":"2021-11-25T15:30:51","modified_gmt":"2021-11-25T06:30:51","slug":"kinetic-resolution-of-racemic-carboxylic-acids-through-asymmetric-protolactonization-promoted-by-chiral-phosphonous-acid-diester","status":"publish","type":"post","link":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/archives\/190","title":{"rendered":"Kinetic Resolution of Racemic Carboxylic Acids through Asymmetric Protolactonization Promoted by Chiral Phosphonous Acid Diester"},"content":{"rendered":"\n<p>Masayuki Sakuma, Akira Sakakura,* Kazuaki Ishihara*&nbsp;<br><em>Org. Lett.<\/em><strong>2013<\/strong>,&nbsp;<em>15<\/em>&nbsp;(11), 2838\u20132841.&nbsp;&nbsp;(published online: May 15, 2013)&nbsp;<br><a href=\"https:\/\/doi.org\/10.1021\/ol401313d\">DOI: 10.1021\/ol401313d&nbsp;<img decoding=\"async\" src=\"http:\/\/www.cc.okayama-u.ac.jp\/~sakakura\/bioorgchem\/_src\/9061\/img20180629093542651479.png\" alt=\"LinkIcon\"><\/a><\/p>\n\n\n\n<figure class=\"wp-block-image size-full is-resized\"><img loading=\"lazy\" decoding=\"async\" src=\"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/08\/protolactonizaation.png\" alt=\"\" class=\"wp-image-191\" width=\"480\" height=\"237\" srcset=\"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/08\/protolactonizaation.png 960w, http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/08\/protolactonizaation-300x148.png 300w, http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/08\/protolactonizaation-768x379.png 768w\" sizes=\"auto, (max-width: 480px) 100vw, 480px\" \/><\/figure>\n\n\n\n<p>Chiral phosphoniumsalts induce the kinetic resolution of racemicR-substituted unsaturated carboxylic acids through asymmetric protolactonization. &nbsp;Both the lactones and the recovered carboxylic acids are obtained with high enantioselectivities and high&nbsp;<em>S<\/em>&nbsp;(=&nbsp;<em>k<\/em>fast\/<em>k<\/em>slow)&nbsp;values&nbsp;. &nbsp;Asymmetric protolactonization also leads to the desymmetrization of achiral carboxylic acids. &nbsp;Notably, chiral phosphonous acid diester not only induced the enantioselectivity but also promoted protolactonization.&nbsp;<\/p>\n\n\n\n<p><\/p>\n\n\n\n<p>This paper was highlighted in&nbsp;<em>Synfacts<\/em><strong> <\/strong><strong>2013<\/strong>,&nbsp;<em>9<\/em>&nbsp;(8), 894. &nbsp;&nbsp;<br>Kinetic Resolution of Unsaturated Carboxylic Acids via Protolactonization&nbsp;<br><a href=\"https:\/\/doi.org\/10.1055\/s-0033-1339441\">DOI: 10.1055\/s-0033-1339441&nbsp;<img decoding=\"async\" src=\"http:\/\/www.cc.okayama-u.ac.jp\/~sakakura\/bioorgchem\/_src\/9062\/img20180629093542651479.png\" alt=\"LinkIcon\"><\/a><\/p>\n","protected":false},"excerpt":{"rendered":"<p>Masayuki Sakuma, Akira Sakakura,* Kazuaki Ishihara*&nbsp;Org. Lett.2013,&nbsp;15&nbsp;(11), 2838\u20132841.&nbsp;&#038;n [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":191,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"vkexunit_cta_each_option":"","footnotes":""},"categories":[6],"tags":[],"class_list":["post-190","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-publications"],"_links":{"self":[{"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/posts\/190","targetHints":{"allow":["GET"]}}],"collection":[{"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/comments?post=190"}],"version-history":[{"count":4,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/posts\/190\/revisions"}],"predecessor-version":[{"id":221,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/posts\/190\/revisions\/221"}],"wp:featuredmedia":[{"embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/media\/191"}],"wp:attachment":[{"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/media?parent=190"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/categories?post=190"},{"taxonomy":"post_tag","embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/tags?post=190"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}