{"id":426,"date":"2020-12-09T21:24:12","date_gmt":"2020-12-09T21:24:12","guid":{"rendered":"https:\/\/info.ias.tuwien.ac.at\/bsc\/?p=426"},"modified":"2020-12-09T21:24:40","modified_gmt":"2020-12-09T21:24:40","slug":"intercepted-dehomologation-of-aldoses-by-n-heterocyclic-carbene-catalysis-a-novel-transformation-in-carbohydrate-chemistry","status":"publish","type":"post","link":"https:\/\/info.ias.tuwien.ac.at\/bsc\/publications\/intercepted-dehomologation-of-aldoses-by-n-heterocyclic-carbene-catalysis-a-novel-transformation-in-carbohydrate-chemistry\/","title":{"rendered":"Intercepted dehomologation of aldoses by N-heterocyclic carbene catalysis \u2013 a novel transformation in carbohydrate chemistry"},"content":{"rendered":"\t\t<div data-elementor-type=\"wp-post\" data-elementor-id=\"426\" class=\"elementor elementor-426\" data-elementor-post-type=\"post\">\n\t\t\t\t\t\t<section class=\"elementor-section elementor-top-section elementor-element elementor-element-6694ee5b elementor-section-full_width elementor-section-height-default elementor-section-height-default\" data-id=\"6694ee5b\" data-element_type=\"section\">\n\t\t\t\t\t\t<div class=\"elementor-container elementor-column-gap-default\">\n\t\t\t\t\t<div class=\"elementor-column elementor-col-100 elementor-top-column elementor-element elementor-element-2a62baf7\" data-id=\"2a62baf7\" data-element_type=\"column\">\n\t\t\t<div class=\"elementor-widget-wrap elementor-element-populated\">\n\t\t\t\t\t\t<div class=\"elementor-element elementor-element-6014ef94 elementor-widget elementor-widget-text-editor\" data-id=\"6014ef94\" data-element_type=\"widget\" data-widget_type=\"text-editor.default\">\n\t\t\t\t<div class=\"elementor-widget-container\">\n\t\t\t\t\t\t\tThe development of an N-heterocyclic carbene (NHC) catalysed intercepted dehomologation of aldoses is reported. The unique selectivity of NHCs for aldehydes is exploited in the complex context of reducing sugars. Examples of strong substrate governance for either intercepted dehomologation or a subsequent redoxlactonisation were identified and mechanistically understood. More importantly, it was shown that catalyst design allowed the tuning of the selectivity of the reaction with structurally unbiased starting materials towards either of the two scenarios.\r\n\r\nAuthors: Markus Draskovits, Hubert Kalaus, Christian Stanetty * and Marko D. Mihovilovic\r\n\r\nDOI: <a href=\"https:\/\/doi.org\/10.1039\/C9CC05906G\" target=\"_blank\" rel=\"noopener noreferrer\">10.1039\/c9cc05906g<\/a>\t\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t\t<\/div>\n\t\t<\/div>\n\t\t\t\t\t<\/div>\n\t\t<\/section>\n\t\t\t\t<\/div>\n\t\t","protected":false},"excerpt":{"rendered":"<p>The development of an N-heterocyclic carbene (NHC) catalysed intercepted dehomologation of aldoses is reported. The unique selectivity of NHCs for aldehydes is exploited in the complex context of reducing sugars. Examples of strong substrate governance for either intercepted dehomologation or a subsequent redoxlactonisation were identified and mechanistically understood. More importantly, it was shown that catalyst [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"site-sidebar-layout":"default","site-content-layout":"default","ast-site-content-layout":"","site-content-style":"default","site-sidebar-style":"default","ast-global-header-display":"","ast-banner-title-visibility":"","ast-main-header-display":"","ast-hfb-above-header-display":"","ast-hfb-below-header-display":"","ast-hfb-mobile-header-display":"","site-post-title":"","ast-breadcrumbs-content":"","ast-featured-img":"","footer-sml-layout":"","theme-transparent-header-meta":"default","adv-header-id-meta":"","stick-header-meta":"default","header-above-stick-meta":"","header-main-stick-meta":"","header-below-stick-meta":"","astra-migrate-meta-layouts":"default","ast-page-background-enabled":"default","ast-page-background-meta":{"desktop":{"background-color":"","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""},"tablet":{"background-color":"","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""},"mobile":{"background-color":"","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""}},"ast-content-background-meta":{"desktop":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""},"tablet":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""},"mobile":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""}},"footnotes":""},"categories":[5],"tags":[11,9],"_links":{"self":[{"href":"https:\/\/info.ias.tuwien.ac.at\/bsc\/wp-json\/wp\/v2\/posts\/426"}],"collection":[{"href":"https:\/\/info.ias.tuwien.ac.at\/bsc\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/info.ias.tuwien.ac.at\/bsc\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/info.ias.tuwien.ac.at\/bsc\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/info.ias.tuwien.ac.at\/bsc\/wp-json\/wp\/v2\/comments?post=426"}],"version-history":[{"count":0,"href":"https:\/\/info.ias.tuwien.ac.at\/bsc\/wp-json\/wp\/v2\/posts\/426\/revisions"}],"wp:attachment":[{"href":"https:\/\/info.ias.tuwien.ac.at\/bsc\/wp-json\/wp\/v2\/media?parent=426"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/info.ias.tuwien.ac.at\/bsc\/wp-json\/wp\/v2\/categories?post=426"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/info.ias.tuwien.ac.at\/bsc\/wp-json\/wp\/v2\/tags?post=426"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}