{"id":155,"date":"2021-11-25T15:43:56","date_gmt":"2021-11-25T06:43:56","guid":{"rendered":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/?p=155"},"modified":"2021-11-25T15:54:16","modified_gmt":"2021-11-25T06:54:16","slug":"a-short-access-to-35-disubstituted-piperazinones-based-on-the-aza-michael-addition-of-%ce%b1-amino-esters-to-%ce%b2-substituted-nitroalkenes","status":"publish","type":"post","link":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/archives\/155","title":{"rendered":"A short access to 3,5-disubstituted piperazinones based on the aza-Michael addition of \u03b1-amino esters to \u03b2-substituted nitroalkenes"},"content":{"rendered":"\n<p>Takayuki Kudoh,* Seiji Isoyama, Sachiko Kagimoto, Katsutoshi Kurihara, Akira Sakakura*&nbsp;<br><em>Tetrahedron Lett.<\/em><strong>2016<\/strong>,&nbsp;<em>57<\/em>&nbsp;(42), 4693\u20134696. &nbsp;(Published online: Sept 16, 2016)&nbsp;<br><a href=\"https:\/\/doi.org\/10.1016\/j.tetlet.2016.09.015\">DOI: 10.1016\/j.tetlet.2016.09.015&nbsp;<img decoding=\"async\" src=\"http:\/\/www.cc.okayama-u.ac.jp\/~sakakura\/bioorgchem\/_src\/9144\/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\/08\/piperazinone-1024x206.png\" alt=\"\" class=\"wp-image-156\" width=\"512\" height=\"103\" srcset=\"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/08\/piperazinone-1024x206.png 1024w, http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/08\/piperazinone-300x60.png 300w, http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/08\/piperazinone-768x154.png 768w, http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/08\/piperazinone.png 1497w\" sizes=\"auto, (max-width: 512px) 100vw, 512px\" \/><\/figure>\n\n\n\n<p>A simple procedure for the synthesis of chiral 3,5-disubstituted piperazinones is described. &nbsp;The aza-Michael addition of \u03b1-amino esters to \u03b2-substituted nitroalkenes in an organic\/aqueous biphasic solvent system followed by reduction of a nitro group with zinc nanopowder in acidic media and intramolecular ester-amide exchange under heating conditions gives piperazinones in good overall yields. &nbsp;This novel three-step process can provide a short access to a variety of chiral 3,5-disubstituted piperazinones simply by changing the combination of starting nitroalkenes and \u03b1-amino esters. &nbsp;This process can be applied to the concise synthesis of the piperazinone-containing natural product 6\u2019,6\u2019\u2019-didebromo-&nbsp;<em>cis<\/em>-3,4-dihydrohamacanthin B.<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Takayuki Kudoh,* Seiji Isoyama, Sachiko Kagimoto, Katsutoshi Kurihara, Akira Sakakura*&nbsp;Tetrahedron Lett.2 [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":156,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"vkexunit_cta_each_option":"","footnotes":""},"categories":[6],"tags":[],"class_list":["post-155","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\/155","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=155"}],"version-history":[{"count":2,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/posts\/155\/revisions"}],"predecessor-version":[{"id":252,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/posts\/155\/revisions\/252"}],"wp:featuredmedia":[{"embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/media\/156"}],"wp:attachment":[{"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/media?parent=155"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/categories?post=155"},{"taxonomy":"post_tag","embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/tags?post=155"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}