{"id":100,"date":"2021-11-25T15:47:00","date_gmt":"2021-11-25T06:47:00","guid":{"rendered":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/?p=100"},"modified":"2021-11-25T16:00:14","modified_gmt":"2021-11-25T07:00:14","slug":"synthesis-of-functionalized-cyclopropylboronic-esters-based-on-a-12-metallate-rearrangement-of-cyclopropenylboronate","status":"publish","type":"post","link":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/archives\/100","title":{"rendered":"Synthesis of functionalized cyclopropylboronic esters based on a 1,2-metallate rearrangement of cyclopropenylboronate"},"content":{"rendered":"\n<p>Haruki Mizoguchi,* Masaya Seriua, Akira Sakakura*&nbsp;<br><em>Chem. Commun.<\/em><strong>2020<\/strong>,&nbsp;<em>56<\/em>&nbsp;(99), 15545\u201315548. (Published online:&nbsp;November&nbsp;18, 2020)&nbsp;<br><a href=\"https:\/\/doi.org\/10.1039\/D0CC07134J\">DOI: 10.1039\/d0cc07134j&nbsp;<img decoding=\"async\" src=\"http:\/\/www.cc.okayama-u.ac.jp\/~sakakura\/bioorgchem\/_src\/10713\/img20180629093542651479.png\" alt=\"LinkIcon\"><\/a><\/p>\n\n\n\n<figure class=\"wp-block-image size-large is-resized\"><img loading=\"lazy\" decoding=\"async\" src=\"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/07\/cyclopropene_cc_ga-1024x389.png\" alt=\"\" class=\"wp-image-101\" width=\"512\" height=\"195\" srcset=\"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/07\/cyclopropene_cc_ga-1024x389.png 1024w, http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/07\/cyclopropene_cc_ga-300x114.png 300w, http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/07\/cyclopropene_cc_ga-768x292.png 768w, http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/07\/cyclopropene_cc_ga-1536x583.png 1536w, http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/07\/cyclopropene_cc_ga-2048x777.png 2048w\" sizes=\"auto, (max-width: 512px) 100vw, 512px\" \/><\/figure>\n\n\n\n<p>A procedure converting tribromocyclopropane to densely functionalized \u03b2-selenocyclopropylboronic ester using the 1,2-metallate rearrangement of a boron ate-complex has been developed.&nbsp; Treatment of an&nbsp;<em>in situ<\/em>-generated cyclopropenylboronic ester ate-complex with phenylselenenyl chloride triggered stereospecific rearrangement to produce functionalized cyclopropanes.&nbsp; DFT calculations for 1,2-metallate rearrangement suggested that the reaction proceeds through a seleniranium intermediate.<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Haruki Mizoguchi,* Masaya Seriua, Akira Sakakura*&nbsp;Chem. Commun.2020,&nbsp;56&nbsp;(99), 15545\u201315548. (Pub [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":101,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"vkexunit_cta_each_option":"","footnotes":""},"categories":[6],"tags":[],"class_list":["post-100","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\/100","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=100"}],"version-history":[{"count":2,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/posts\/100\/revisions"}],"predecessor-version":[{"id":268,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/posts\/100\/revisions\/268"}],"wp:featuredmedia":[{"embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/media\/101"}],"wp:attachment":[{"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/media?parent=100"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/categories?post=100"},{"taxonomy":"post_tag","embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/tags?post=100"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}