{"id":165,"date":"2021-11-25T15:43:31","date_gmt":"2021-11-25T06:43:31","guid":{"rendered":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/?p=165"},"modified":"2021-11-25T15:53:26","modified_gmt":"2021-11-25T06:53:26","slug":"enantioselective-13-dipolar-cycloaddition-of-azomethine-imines-with-propioloylpyrazoles-induced-by-chiral-%cf%80%e2%88%92cation-catalysts","status":"publish","type":"post","link":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/archives\/165","title":{"rendered":"Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Imines with Propioloylpyrazoles Induced by Chiral \u03c0\u2212Cation Catalysts"},"content":{"rendered":"\n<p>Masahiro Hori, Akira Sakakura,* Kazuaki Ishihara*&nbsp;<br><em>J. Am. Chem. Soc.<\/em><strong>2014<\/strong>,&nbsp;<em>136<\/em>&nbsp;(38), 13198\u201313201. &nbsp;(Published online: Sept 16, 2014)&nbsp;<br><a href=\"https:\/\/doi.org\/10.1021\/ja508441t\">DOI: 10.1021\/ja508441t&nbsp;<img decoding=\"async\" src=\"http:\/\/www.cc.okayama-u.ac.jp\/~sakakura\/bioorgchem\/_src\/9147\/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\/pi-cation_imine.png\" alt=\"\" class=\"wp-image-166\" width=\"480\" height=\"197\" srcset=\"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/08\/pi-cation_imine.png 960w, http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/08\/pi-cation_imine-300x123.png 300w, http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/08\/pi-cation_imine-768x315.png 768w\" sizes=\"auto, (max-width: 480px) 100vw, 480px\" \/><\/figure>\n\n\n\n<p>We developed 1,3-dipolar cycloadditions of azomethine imines with propioloylpyrazoles catalyzed by a chiral copper(II) complex of 3-(2-naphthyl)-l-alanine amide. &nbsp;The asymmetric environment created by intramolecular \u03c0\u2013cation interaction and the N-alkyl group of the chiral ligand gives the corresponding adducts in high yields with excellent enantioselectivity. &nbsp;This is the first successful method for the catalytic enantioselective 1,3-dipolar cycloaddition of azomethine imines with internal alkyne derivatives to give fully substituted pyrazolines.&nbsp;<\/p>\n\n\n\n<p><\/p>\n\n\n\n<p>This paper was highlighted in&nbsp;&nbsp;<em>Synfacts<\/em><strong>2014<\/strong>,&nbsp;<em>10<\/em>&nbsp;(12), 1288. &nbsp;&nbsp;<br>Synthesis of Chiral Pyrazolines via Chiral \u03c0-Cation Catalysis&nbsp;<br><a href=\"https:\/\/doi.org\/10.1055\/s-0034-1379534\">DOI: 10.1055\/s-0034-1379534&nbsp;<img decoding=\"async\" src=\"http:\/\/www.cc.okayama-u.ac.jp\/~sakakura\/bioorgchem\/_src\/9148\/img20180629093542651479.png\" alt=\"LinkIcon\"><\/a><\/p>\n","protected":false},"excerpt":{"rendered":"<p>Masahiro Hori, Akira Sakakura,* Kazuaki Ishihara*&nbsp;J. Am. Chem. Soc.2014,&nbsp;136&nbsp;(38), 13198\u201313201. [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":166,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"vkexunit_cta_each_option":"","footnotes":""},"categories":[6],"tags":[],"class_list":["post-165","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\/165","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=165"}],"version-history":[{"count":2,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/posts\/165\/revisions"}],"predecessor-version":[{"id":250,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/posts\/165\/revisions\/250"}],"wp:featuredmedia":[{"embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/media\/166"}],"wp:attachment":[{"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/media?parent=165"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/categories?post=165"},{"taxonomy":"post_tag","embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/tags?post=165"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}