{"id":122,"date":"2021-11-25T15:45:57","date_gmt":"2021-11-25T06:45:57","guid":{"rendered":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/?p=122"},"modified":"2021-11-25T15:57:52","modified_gmt":"2021-11-25T06:57:52","slug":"enantioselective-13-dipolar-cycloaddition-reaction-of-nitrones-with-%ce%b1-acyloxyacroleins-catalyzed-by-dipeptide-derived-chiral-tri-or-diammonium-salts","status":"publish","type":"post","link":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/archives\/122","title":{"rendered":"Enantioselective 1,3-Dipolar Cycloaddition Reaction of Nitrones with \u03b1-(Acyloxy)acroleins Catalyzed by Dipeptide-Derived Chiral Tri- or Diammonium Salts"},"content":{"rendered":"\n<p>Chihiro Kidou, Haruki Mizoguchi,&nbsp;Tatsuo Nehira, Akira Sakakura*&nbsp;<br><em>Synlett&nbsp;<\/em><strong>2019<\/strong>,&nbsp;<em>30<\/em>&nbsp;(15), 1835\u20131839.&nbsp; (Published online: July&nbsp;&nbsp;30, 2019)&nbsp;<br><a href=\"https:\/\/doi.org\/10.1055\/s-0039-1690133\">DOI: 10.1055\/s-0039-1690133&nbsp;<img decoding=\"async\" src=\"http:\/\/www.cc.okayama-u.ac.jp\/~sakakura\/bioorgchem\/_src\/9577\/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\/07\/32nitrone.png\" alt=\"\" class=\"wp-image-123\" width=\"480\" height=\"249\" srcset=\"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/07\/32nitrone.png 960w, http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/07\/32nitrone-300x156.png 300w, http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/07\/32nitrone-768x398.png 768w\" sizes=\"auto, (max-width: 480px) 100vw, 480px\" \/><\/figure>\n\n\n\n<p>Organoammonium salts of dipeptide-derived chiral triamines or diamines with TfOH catalyzed the enantioselective 1,3-dipolar cycloaddition reactions of \u03b1-acyloxyacroleins with nitrones to give the corresponding adducts in good yields (up to 96%) and with high diastereo- and enantioselectivities (up to 89% ee). Although \u03b1-(&nbsp;<em>p<\/em>-methoxybenzoyloxy)acrolein is rather unstable under the reaction conditions, \u03b1-(3-pyrroline-1-carbonyloxy)acrolein is stable enough to be smoothly converted into the corresponding adducts with the aid of the chiral organoammonium salt catalysts.<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Chihiro Kidou, Haruki Mizoguchi,&nbsp;Tatsuo Nehira, Akira Sakakura*&nbsp;Synlett&nbsp;2019,&nbsp;30&nbsp;(15) [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":123,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"vkexunit_cta_each_option":"","footnotes":""},"categories":[6],"tags":[],"class_list":["post-122","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\/122","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=122"}],"version-history":[{"count":2,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/posts\/122\/revisions"}],"predecessor-version":[{"id":262,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/posts\/122\/revisions\/262"}],"wp:featuredmedia":[{"embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/media\/123"}],"wp:attachment":[{"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/media?parent=122"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/categories?post=122"},{"taxonomy":"post_tag","embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/tags?post=122"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}