{"id":168,"date":"2021-11-25T15:43:23","date_gmt":"2021-11-25T06:43:23","guid":{"rendered":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/?p=168"},"modified":"2021-11-25T15:52:48","modified_gmt":"2021-11-25T06:52:48","slug":"cooperative-activation-with-chiral-nucleophilic-catalysts-and-n-haloimides-enantioselective-iodolactonization-of-4-arylmethyl-4-pentenoic-acids","status":"publish","type":"post","link":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/archives\/168","title":{"rendered":"Cooperative Activation with Chiral Nucleophilic Catalysts and N-Haloimides: Enantioselective Iodolactonization of 4-Arylmethyl-4-pentenoic Acids"},"content":{"rendered":"\n<p>Hidefumi Nakatsuji, Yasuhiro Sawamura, Akira Sakakura,* Kazuaki Ishihara*&nbsp;<br><em>Angew. Chem. Int. Ed.<\/em><strong>2014<\/strong>,&nbsp;<em>53<\/em>&nbsp;(27), 6974\u20136977. &nbsp;(Published online: 19 May 2014)&nbsp;<br><a href=\"https:\/\/doi.org\/10.1002\/anie.201400946\">DOI: 10.1002\/anie.201400946&nbsp;<img decoding=\"async\" src=\"http:\/\/www.cc.okayama-u.ac.jp\/~sakakura\/bioorgchem\/_src\/9149\/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\/iodolactonization.png\" alt=\"\" class=\"wp-image-169\" width=\"480\" height=\"229\" srcset=\"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/08\/iodolactonization.png 960w, http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/08\/iodolactonization-300x143.png 300w, http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/08\/iodolactonization-768x366.png 768w\" sizes=\"auto, (max-width: 480px) 100vw, 480px\" \/><\/figure>\n\n\n\n<p><strong>Active duty:<\/strong>&nbsp; Chiral triaryl phosphates promote the enantioselective iodolactonization of 4-substituted 4-pentenoic acids to give the corresponding iodolactones in high yields with high enantioselectivity (see scheme). &nbsp;&nbsp;<em>N<\/em>-Chlorophthalimide (NCP) is employed as a Lewis acidic activator and oxidant of I2 for the present iodolactonization. &nbsp;In combination with 1.5 equivalents of NCP, only 0.5 equivalents of I2 are sufficient for generating the iodinating reagent.&nbsp;<\/p>\n\n\n\n<p><\/p>\n\n\n\n<p>This paper was highlighted in&nbsp;<em>Synfacts<\/em><strong>2014<\/strong>&nbsp;,&nbsp;<em>10<\/em>&nbsp;(8),&nbsp;&nbsp;0874. &nbsp;&nbsp;<br>Enantioselective Iodolactonization by Cooperative Activation&nbsp;<br><a href=\"https:\/\/doi.org\/10.1055\/s-0034-1378508\">DOI: 10.1055\/s-0034-1378508&nbsp;<img decoding=\"async\" src=\"http:\/\/www.cc.okayama-u.ac.jp\/~sakakura\/bioorgchem\/_src\/9150\/img20180629093542651479.png\" alt=\"LinkIcon\"><\/a><\/p>\n","protected":false},"excerpt":{"rendered":"<p>Hidefumi Nakatsuji, Yasuhiro Sawamura, Akira Sakakura,* Kazuaki Ishihara*&nbsp;Angew. Chem. Int. Ed.2014,&#038;nbsp [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":169,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"vkexunit_cta_each_option":"","footnotes":""},"categories":[6],"tags":[],"class_list":["post-168","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\/168","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=168"}],"version-history":[{"count":2,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/posts\/168\/revisions"}],"predecessor-version":[{"id":249,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/posts\/168\/revisions\/249"}],"wp:featuredmedia":[{"embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/media\/169"}],"wp:attachment":[{"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/media?parent=168"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/categories?post=168"},{"taxonomy":"post_tag","embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/tags?post=168"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}