{"id":294,"date":"2022-04-06T14:09:23","date_gmt":"2022-04-06T05:09:23","guid":{"rendered":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/?p=294"},"modified":"2022-04-06T14:18:35","modified_gmt":"2022-04-06T05:18:35","slug":"enantioselective-construction-of-%ce%b2-hydroxy-%ce%b1%ce%b1-disubstituted-%ce%b1-amino-acid-derivatives-via-direct-aldol-reaction-of-%ce%b1-imino-esters","status":"publish","type":"post","link":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/archives\/294","title":{"rendered":"Enantioselective construction of \u03b2-hydroxy-\u03b1,\u03b1-disubstituted \u03b1-amino acid derivatives via direct aldol reaction of \u03b1-imino esters"},"content":{"rendered":"\n<p>Yuya Araki, Masato Hanada, Yoshiko Iguchi, Haruki Mizoguchi, Akira Sakakura*<br><em>Tetrahedron<\/em>, in Press <br>DOI: <a rel=\"noreferrer noopener\" href=\"https:\/\/doi.org\/10.1016\/j.tet.2022.132695\" target=\"_blank\">10.1016\/j.tet.2022.132695<\/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\/2022\/04\/1-s2.0-S0040402022000813-ga1_lrg-1024x204.jpg\" alt=\"\" class=\"wp-image-295\" width=\"768\" height=\"153\" srcset=\"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2022\/04\/1-s2.0-S0040402022000813-ga1_lrg-1024x204.jpg 1024w, http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2022\/04\/1-s2.0-S0040402022000813-ga1_lrg-300x60.jpg 300w, http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2022\/04\/1-s2.0-S0040402022000813-ga1_lrg-768x153.jpg 768w, http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2022\/04\/1-s2.0-S0040402022000813-ga1_lrg-1536x305.jpg 1536w, http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2022\/04\/1-s2.0-S0040402022000813-ga1_lrg-2048x407.jpg 2048w\" sizes=\"auto, (max-width: 768px) 100vw, 768px\" \/><\/figure>\n\n\n\n<p>The \u03b2-hydroxy-\u03b1,\u03b1-disubstituted \u03b1-amino acid is a valuable&nbsp;structural motif&nbsp;for research in the field of bioorganic chemistry and in the development of peptide drugs. This report describes the enantioselective direct-aldol reaction of \u03b1-imino esters with&nbsp;glyoxylate&nbsp;esters. We discovered that a catalytic amount of Co(OAc)<sub>2<\/sub>-pybox complex catalyzed the&nbsp;aldol reaction&nbsp;of salicylaldehyde-derived \u03b1-imino esters with benzyl glyoxylate in good yield and&nbsp;enantioselectivity. In addition,&nbsp;hydrolysis&nbsp;of the&nbsp;imine&nbsp;moiety of the aldol products followed by Boc protection of the resultant&nbsp;amino group&nbsp;gave the&nbsp;<em>N<\/em>-Boc-protected&nbsp;amino acid derivatives.<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Yuya Araki, Masato Hanada, Yoshiko Iguchi, Haruki Mizoguchi, Akira Sakakura*Tetrahedron, in Press DOI: 10.1016 [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":295,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"vkexunit_cta_each_option":"","footnotes":""},"categories":[6],"tags":[],"class_list":["post-294","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\/294","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=294"}],"version-history":[{"count":3,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/posts\/294\/revisions"}],"predecessor-version":[{"id":301,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/posts\/294\/revisions\/301"}],"wp:featuredmedia":[{"embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/media\/295"}],"wp:attachment":[{"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/media?parent=294"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/categories?post=294"},{"taxonomy":"post_tag","embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/tags?post=294"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}