{"id":1620,"date":"2025-06-26T20:41:57","date_gmt":"2025-06-26T23:41:57","guid":{"rendered":"https:\/\/cormanich.iqm.unicamp.br\/?p=1620"},"modified":"2025-06-26T20:41:57","modified_gmt":"2025-06-26T23:41:57","slug":"new-paper-in-obc-with-coelhos-lab","status":"publish","type":"post","link":"https:\/\/cormanich.iqm.unicamp.br\/?p=1620","title":{"rendered":"New paper in OBC with Coelho&#8217;s Lab"},"content":{"rendered":"\n<p class=\"wp-block-paragraph\">We are pleased to share our latest collaborative work with Professor Fernando Coelho\u2019s group, now published in <em>Organic &amp; Biomolecular Chemistry<\/em>:<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>\u201cAn asymmetric and theoretical approach to the Morita\u2013Baylis\u2013Hillman reaction using vinyl-1,2,4-oxadiazoles as nucleophiles\u201d<\/strong><br>\u2020 Thaynan A. B. Chagas, Bruno A. Piscelli, Hugo Santos, S\u00e2mia R. Lima, Rodrigo A. Cormanich,* F\u00e1bio S. Fernandes,* and Fernando Coelho*<br><a>https:\/\/doi.org\/10.1039\/d5ob00540j<\/a><\/p>\n\n\n\n<p class=\"wp-block-paragraph\">In this study, we report the first enantioselective Morita\u2013Baylis\u2013Hillman (MBH) reaction using a vinyl heterocycle as the nucleophile. Catalyzed by \u03b2-isocupreidine (\u03b2-ICD), the reaction between vinyl-1,2,4-oxadiazoles and N-substituted isatins delivers highly functionalized products with yields up to 95% and excellent enantiomeric ratios (up to 98:2 er).<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">Computational studies could elucidate the origin of enantioselectivity and the preference for the <em>R<\/em> enantiomer. These insights also shed light on the lack of selectivity observed with nitro-substituted isatins.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">Importantly, this strategy enabled access to chiral analogues of the natural products phidianidine A and <strong>B<\/strong>, offering a promising route for generating novel chiral 1,2,4-oxadiazoles.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">Congratulations to the students Thaynan and bruno and all involved in this exciting collaboration!<\/p>\n","protected":false},"excerpt":{"rendered":"<p>We are pleased to share our latest collaborative work with Professor Fernando Coelho\u2019s group, now published in Organic &amp; Biomolecular Chemistry: \u201cAn asymmetric and theoretical approach to the Morita\u2013Baylis\u2013Hillman reaction using vinyl-1,2,4-oxadiazoles as nucleophiles\u201d\u2020 Thaynan A. B. Chagas, Bruno A. Piscelli, Hugo Santos, S\u00e2mia R. Lima, Rodrigo A. Cormanich,* F\u00e1bio S. Fernandes,* and Fernando Coelho*https:\/\/doi.org\/10.1039\/d5ob00540j&#8230;<\/p>\n","protected":false},"author":1,"featured_media":1622,"comment_status":"closed","ping_status":"","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[4],"tags":[],"class_list":["post-1620","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-post"],"_links":{"self":[{"href":"https:\/\/cormanich.iqm.unicamp.br\/index.php?rest_route=\/wp\/v2\/posts\/1620","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/cormanich.iqm.unicamp.br\/index.php?rest_route=\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/cormanich.iqm.unicamp.br\/index.php?rest_route=\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/cormanich.iqm.unicamp.br\/index.php?rest_route=\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/cormanich.iqm.unicamp.br\/index.php?rest_route=%2Fwp%2Fv2%2Fcomments&post=1620"}],"version-history":[{"count":1,"href":"https:\/\/cormanich.iqm.unicamp.br\/index.php?rest_route=\/wp\/v2\/posts\/1620\/revisions"}],"predecessor-version":[{"id":1623,"href":"https:\/\/cormanich.iqm.unicamp.br\/index.php?rest_route=\/wp\/v2\/posts\/1620\/revisions\/1623"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/cormanich.iqm.unicamp.br\/index.php?rest_route=\/wp\/v2\/media\/1622"}],"wp:attachment":[{"href":"https:\/\/cormanich.iqm.unicamp.br\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=1620"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/cormanich.iqm.unicamp.br\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=1620"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/cormanich.iqm.unicamp.br\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=1620"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}