{"id":135,"date":"2021-11-25T15:45:02","date_gmt":"2021-11-25T06:45:02","guid":{"rendered":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/?p=135"},"modified":"2021-11-25T15:56:10","modified_gmt":"2021-11-25T06:56:10","slug":"enantioselective-aza-friedel-crafts-reaction-of-furan-with-%ce%b1-ketimino-esters-induced-by-a-conjugated-double-hydrogen-bond-network-of-chiral-bisphosphoric-acid-catalysts","status":"publish","type":"post","link":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/archives\/135","title":{"rendered":"Enantioselective aza-Friedel\u2013Crafts reaction of furan with \u03b1-ketimino esters induced by a conjugated double hydrogen bond network of chiral bis(phosphoric acid) catalysts"},"content":{"rendered":"\n<p>Manabu Hatano, &nbsp;Haruka Okamoto, &nbsp;Taro Kawakami, &nbsp;Kohei Toh, &nbsp;Hidefumi Nakatsuji, &nbsp;Akira Sakakura,*&nbsp; Kazuaki Ishihara*&nbsp;&nbsp;<br><em>Chem. Sci.<\/em><strong>2018<\/strong>,&nbsp;<em>9<\/em>&nbsp;(30), 6361\u20136367.&nbsp; (Published online:&nbsp;June 25, 2018)&nbsp;<br><a href=\"https:\/\/doi.org\/10.1039\/C8SC02290A\">DOI: 10.1039\/C8SC02290A&nbsp;<img decoding=\"async\" src=\"http:\/\/www.cc.okayama-u.ac.jp\/~sakakura\/bioorgchem\/_src\/9287\/img20180629093542651479.png\" alt=\"LinkIcon\"><\/a><\/p>\n\n\n\n<figure class=\"wp-block-image size-full\"><img loading=\"lazy\" decoding=\"async\" width=\"293\" height=\"189\" src=\"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/07\/bisphosphoric_acid.gif\" alt=\"\" class=\"wp-image-136\"\/><\/figure>\n\n\n\n<p>Chiral&nbsp;<em>C<\/em>2- and&nbsp;<em>C<\/em>1-symmetric BINOL-derived bis(phosphoric acid) catalysts, which have OP(=O)(OH)2\/OP(=O)(OH)(OR) moieties at the 2,2\u2032-positions, were developed and used for the enantioselective aza-Friedel\u2013Crafts reaction of 2-methoxyfuran with \u03b1-ketimino esters for the first time. &nbsp;The intramolecular conjugated double hydrogen bond network is a key to increasing the Br\u00f8nsted acidity and preventing deactivation of the catalysts. &nbsp;Highly functionalized \u03b1-amino acid derivatives with a chiral quaternary carbon center could be transformed into versatile optically active&nbsp;<em>N<\/em>- and&nbsp;<em>O<\/em>-heterocycles and an \u03b1-aryl-substituted serine.<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Manabu Hatano, &nbsp;Haruka Okamoto, &nbsp;Taro Kawakami, &nbsp;Kohei Toh, &nbsp;Hidefumi Nakatsuji, &nbsp;Aki [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":133,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"vkexunit_cta_each_option":"","footnotes":""},"categories":[6],"tags":[],"class_list":["post-135","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\/135","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=135"}],"version-history":[{"count":2,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/posts\/135\/revisions"}],"predecessor-version":[{"id":258,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/posts\/135\/revisions\/258"}],"wp:featuredmedia":[{"embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/media\/133"}],"wp:attachment":[{"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/media?parent=135"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/categories?post=135"},{"taxonomy":"post_tag","embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/tags?post=135"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}