{"id":18613,"date":"2022-01-10T20:00:49","date_gmt":"2022-01-10T19:00:49","guid":{"rendered":"https:\/\/www.hilase.cz\/?p=18613"},"modified":"2024-05-21T11:14:04","modified_gmt":"2024-05-21T09:14:04","slug":"stereoselective-cyclopropanation-of-boron-dipyrromethene-bodipy-derivatives-by-an-organocascade-reaction","status":"publish","type":"post","link":"https:\/\/www.hilase.cz\/en\/stereoselective-cyclopropanation-of-boron-dipyrromethene-bodipy-derivatives-by-an-organocascade-reaction\/","title":{"rendered":"Stereoselective Cyclopropanation of Boron Dipyrromethene (BODIPY) Derivatives by an Organocascade Reaction"},"content":{"rendered":"","protected":false},"excerpt":{"rendered":"","protected":false},"author":15,"featured_media":0,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"_monsterinsights_skip_tracking":false,"_monsterinsights_sitenote_active":false,"_monsterinsights_sitenote_note":"","_monsterinsights_sitenote_category":0,"footnotes":""},"categories":[176],"class_list":["post-18613","post","type-post","status-publish","format-standard","hentry","category-paper"],"acf":{"obrazek":{"ID":18617,"id":18617,"title":"Hrabovsky paper (314 x 166 px)","filename":"Hrabovsky-paper-314-x-166-px.png","filesize":80577,"url":"https:\/\/www.hilase.cz\/wp-content\/uploads\/Hrabovsky-paper-314-x-166-px.png","link":"https:\/\/www.hilase.cz\/en\/stereoselective-cyclopropanation-of-boron-dipyrromethene-bodipy-derivatives-by-an-organocascade-reaction\/hrabovsky-paper-314-x-166-px\/","alt":"","author":"15","description":"","caption":"","name":"hrabovsky-paper-314-x-166-px","status":"inherit","uploaded_to":18613,"date":"2022-01-10 15:31:42","modified":"2022-01-10 15:31:42","menu_order":0,"mime_type":"image\/png","type":"image","subtype":"png","icon":"https:\/\/www.hilase.cz\/wp-includes\/images\/media\/default.png","width":314,"height":166,"sizes":{"thumbnail":"https:\/\/www.hilase.cz\/wp-content\/uploads\/Hrabovsky-paper-314-x-166-px-175x166.png","thumbnail-width":175,"thumbnail-height":166,"medium":"https:\/\/www.hilase.cz\/wp-content\/uploads\/Hrabovsky-paper-314-x-166-px.png","medium-width":314,"medium-height":166,"medium_large":"https:\/\/www.hilase.cz\/wp-content\/uploads\/Hrabovsky-paper-314-x-166-px.png","medium_large-width":314,"medium_large-height":166,"large":"https:\/\/www.hilase.cz\/wp-content\/uploads\/Hrabovsky-paper-314-x-166-px.png","large-width":314,"large-height":166,"1536x1536":"https:\/\/www.hilase.cz\/wp-content\/uploads\/Hrabovsky-paper-314-x-166-px.png","1536x1536-width":314,"1536x1536-height":166,"2048x2048":"https:\/\/www.hilase.cz\/wp-content\/uploads\/Hrabovsky-paper-314-x-166-px.png","2048x2048-width":314,"2048x2048-height":166,"image":"https:\/\/www.hilase.cz\/wp-content\/uploads\/Hrabovsky-paper-314-x-166-px.png","image-width":314,"image-height":166,"gallery":"https:\/\/www.hilase.cz\/wp-content\/uploads\/Hrabovsky-paper-314-x-166-px-273x166.png","gallery-width":273,"gallery-height":166,"card":"https:\/\/www.hilase.cz\/wp-content\/uploads\/Hrabovsky-paper-314-x-166-px.png","card-width":314,"card-height":166,"square":"https:\/\/www.hilase.cz\/wp-content\/uploads\/Hrabovsky-paper-314-x-166-px.png","square-width":314,"square-height":166}},"obsah":[{"acf_fc_layout":"text","text":"<p><strong>Our colleague Jan Hrabovsky is a co-author of an article on <em>Stereoselective Cyclopropanation of Boron Dipyrromethene (BODIPY) Derivatives by an Organocascade Reaction<\/em> published in the journal of <a href=\"https:\/\/onlinelibrary.wiley.com\/journal\/16154169\">Advanced Synthesis &amp; Catalysis<\/a>.<\/strong><\/p>\n<p><img decoding=\"async\" src=\"https:\/\/www.hilase.cz\/wp-content\/uploads\/1-45.png\" alt=\"\" \/><br \/>\nThe synthesis of enantiopure chiral boron dipyrromethenes (BODIPYs) is of importance due the intrinsic properties of BODIPYs as fluorophores that could be used as probes for molecular sensing. The present study reports an asymmetric organocatalytic cascade reaction of\u00a0<i>meso<\/i>-chloromethyl BODIPY derivatives with\u00a0<i>\u03b1<\/i>,<i>\u03b2<\/i>-unsaturated aldehydes catalyzed by a chiral secondary amine. The corresponding BODIPY-derived cyclopropanes were produced in isolated yields 66\u201398%, and with diastereomeric ratios 3\/2-&gt;20\/1, and 92\u201399%\u00a0<i>ee<\/i>\u00a0for major diastereomer. The synthetic utility of the protocol was exemplified on a set of additional transformations of the corresponding optically pure compounds. In addition, a study explaining the reaction mechanism (DFT computations) and photophysical characterization of all enantioenriched products were accomplished.<\/p>\n<p><a href=\"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/adsc.202101286\">Learn more.<\/a><\/p>\n","oddelovace":"none"}]},"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v23.9 - https:\/\/yoast.com\/wordpress\/plugins\/seo\/ -->\n<title>Stereoselective Cyclopropanation of Boron Dipyrromethene (BODIPY) Derivatives by an Organocascade Reaction - HiLASE<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/www.hilase.cz\/en\/stereoselective-cyclopropanation-of-boron-dipyrromethene-bodipy-derivatives-by-an-organocascade-reaction\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Stereoselective Cyclopropanation of Boron Dipyrromethene (BODIPY) Derivatives by an Organocascade Reaction - HiLASE\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.hilase.cz\/en\/stereoselective-cyclopropanation-of-boron-dipyrromethene-bodipy-derivatives-by-an-organocascade-reaction\/\" \/>\n<meta property=\"og:site_name\" content=\"HiLASE\" \/>\n<meta property=\"article:published_time\" content=\"2022-01-10T19:00:49+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2024-05-21T09:14:04+00:00\" \/>\n<meta name=\"author\" content=\"Lucka \u0160t\u011bp\u00e1nkov\u00e1\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<meta name=\"twitter:label1\" content=\"Written by\" \/>\n\t<meta name=\"twitter:data1\" content=\"Lucka \u0160t\u011bp\u00e1nkov\u00e1\" \/>\n<script type=\"application\/ld+json\" class=\"yoast-schema-graph\">{\"@context\":\"https:\/\/schema.org\",\"@graph\":[{\"@type\":\"WebPage\",\"@id\":\"https:\/\/www.hilase.cz\/en\/stereoselective-cyclopropanation-of-boron-dipyrromethene-bodipy-derivatives-by-an-organocascade-reaction\/\",\"url\":\"https:\/\/www.hilase.cz\/en\/stereoselective-cyclopropanation-of-boron-dipyrromethene-bodipy-derivatives-by-an-organocascade-reaction\/\",\"name\":\"Stereoselective Cyclopropanation of Boron Dipyrromethene (BODIPY) Derivatives by an Organocascade Reaction - 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