{"id":106,"date":"2021-11-25T15:46:40","date_gmt":"2021-11-25T06:46:40","guid":{"rendered":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/?p=106"},"modified":"2021-11-25T15:59:16","modified_gmt":"2021-11-25T06:59:16","slug":"enantioselective-diels-alder-reaction-of-3-nitrocoumarins-promoted-by-chiral-organoammonium-salt-catalysts","status":"publish","type":"post","link":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/archives\/106","title":{"rendered":"Enantioselective Diels\u2013Alder Reaction of 3-Nitrocoumarins Promoted by Chiral Organoammonium Salt Catalysts"},"content":{"rendered":"\n<p>Yudai Fujii, Ryota Nakao, Saki Sugihara, Keita Fujita, Yuya Araki, Takayuki Kudoh, Ichiro Hayakawa, Haruki Mizoguchi, Akira Sakakura*&nbsp;<br><em>Synlett<\/em><strong>2020<\/strong>,&nbsp;<em>31<\/em>&nbsp;(20), 2013\u20132017. (Published online: October 7, 2020)&nbsp;<br><a href=\"https:\/\/doi.org\/10.1055\/s-0040-1707302\">DOI: 10.1055\/s-0040-1707302&nbsp;<img decoding=\"async\" src=\"http:\/\/www.cc.okayama-u.ac.jp\/~sakakura\/bioorgchem\/_src\/10562\/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\/nitrocoumarin-da-1024x503.png\" alt=\"\" class=\"wp-image-107\" width=\"512\" height=\"252\" srcset=\"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/07\/nitrocoumarin-da-1024x503.png 1024w, http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/07\/nitrocoumarin-da-300x147.png 300w, http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/07\/nitrocoumarin-da-768x377.png 768w, http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/07\/nitrocoumarin-da-1536x754.png 1536w, http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/07\/nitrocoumarin-da.png 1738w\" sizes=\"auto, (max-width: 512px) 100vw, 512px\" \/><\/figure>\n\n\n\n<p>An enantioselective Diels\u2013Alder reaction of 3-nitrocoumarins has been developed.&nbsp; A tryptophan-derived&nbsp;<em>C<\/em>1-symmetric organoammonium thiourea catalyst promoted the reaction of 3-nitrocoumarins with Danishefsky\u2019s diene to give the corresponding adducts with good enantioselectivity (up to 94% ee).&nbsp; One of the resulting adducts was converted into a chiral carbocyclic quaternary \u03b2-amino alcohol.&nbsp;<\/p>\n\n\n\n<p><\/p>\n\n\n\n<p>\u25b6\ufe0e Front Cover<\/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\/cover-synlett-20-2020.png\" alt=\"\" class=\"wp-image-108\" width=\"384\" height=\"512\" srcset=\"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/07\/cover-synlett-20-2020.png 768w, http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/07\/cover-synlett-20-2020-225x300.png 225w\" sizes=\"auto, (max-width: 384px) 100vw, 384px\" \/><\/figure>\n","protected":false},"excerpt":{"rendered":"<p>Yudai Fujii, Ryota Nakao, Saki Sugihara, Keita Fujita, Yuya Araki, Takayuki Kudoh, Ichiro Hayakawa, Haruki Miz [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":108,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"vkexunit_cta_each_option":"","footnotes":""},"categories":[6],"tags":[],"class_list":["post-106","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\/106","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=106"}],"version-history":[{"count":2,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/posts\/106\/revisions"}],"predecessor-version":[{"id":266,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/posts\/106\/revisions\/266"}],"wp:featuredmedia":[{"embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/media\/108"}],"wp:attachment":[{"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/media?parent=106"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/categories?post=106"},{"taxonomy":"post_tag","embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/tags?post=106"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}