{"id":505,"date":"2020-02-14T14:31:11","date_gmt":"2020-02-14T13:31:11","guid":{"rendered":"https:\/\/sites.unimi.it\/apisgroup\/?p=505"},"modified":"2022-01-21T13:07:54","modified_gmt":"2022-01-21T12:07:54","slug":"stereoselective-synthesis-of-%ce%b1%ce%b1%e2%80%b2-dihydroxy-%e2%80%b2beta-beta-diaryl-amino-acids-by-mannich-like-condensation-of-hydroarylamides","status":"publish","type":"post","link":"https:\/\/sites.unimi.it\/apisgroup\/2020\/02\/14\/stereoselective-synthesis-of-%ce%b1%ce%b1%e2%80%b2-dihydroxy-%e2%80%b2beta-beta-diaryl-amino-acids-by-mannich-like-condensation-of-hydroarylamides\/","title":{"rendered":"Stereoselective Synthesis of \u03b1,\u03b1\u2032-Dihydroxy-beta, beta\u2032-diaryl-beta-amino Acids by Mannich-Like Condensation of Hydroarylamides"},"content":{"rendered":"\n<p class=\"wp-block-paragraph\"> Dual \u03b1,\u03b1\u2032-Dihydroxy-beta,beta&#8217;-beta-amino acids are highly interesting tools for several industrial applications. Nevertheless, only few derivatives are reported in the literature and knowledge concerning the substitution pattern as well as their enantioselective syntheses are lacking. Herein, we report on the preparation of enantiopure \u03b1,\u03b1\u2032-dihydroxy-,\u2032-diaryl&#8211;amino acid (dual) derivatives by an efficient Mannich-like condensation of hydroarylamides with 5,6-diethoxy-5,6-dimethyl-1,4-di  oxan-2-one (triethylsilyl)ketene acetal. The synthetic protocol has been optimized affording the dual compounds in very good yields and with different aryl substitution patterns. Taking advantage of the \u201cdouble stereodifferentiation\u201d concept, a highly stereoselective reaction was performed: of the 16 possible isomers, only two diastereoisomers (d.r. up to 93:7) formed. Insights into the high stereocontrol of this condensation were given. <\/p>\n\n\n\n<p class=\"wp-block-paragraph\"> DOI: 10.1002\/ejoc.201901325 <\/p>\n","protected":false},"excerpt":{"rendered":"<p>Dual \u03b1,\u03b1\u2032-Dihydroxy-beta,beta&#8217;-beta-amino acids are highly interesting tools for several industrial applications. Nevertheless, only few derivatives are reported in the literature and knowledge concerning the substitution pattern as well as their enantioselective syntheses are lacking.&#46;&#46;&#46;<\/p>\n","protected":false},"author":1,"featured_media":506,"comment_status":"closed","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[6,7],"tags":[34],"class_list":["post-505","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-application","category-amino-acid","tag-mannich-like"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v28.5 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Stereoselective Synthesis of \u03b1,\u03b1\u2032-Dihydroxy-beta, beta\u2032-diaryl-beta-amino Acids by Mannich-Like Condensation of Hydroarylamides - APIS group<\/title>\n<meta name=\"robots\" content=\"noindex, follow\" \/>\n<meta property=\"og:locale\" content=\"it_IT\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Stereoselective Synthesis of \u03b1,\u03b1\u2032-Dihydroxy-beta, beta\u2032-diaryl-beta-amino Acids by Mannich-Like Condensation of Hydroarylamides - APIS group\" \/>\n<meta property=\"og:description\" content=\"Dual \u03b1,\u03b1\u2032-Dihydroxy-beta,beta&#8217;-beta-amino acids are highly interesting tools for several industrial applications. Nevertheless, only few derivatives are reported in the literature and knowledge concerning the substitution pattern as well as their enantioselective syntheses are lacking.&#046;&#046;&#046;\" \/>\n<meta property=\"og:url\" content=\"https:\/\/sites.unimi.it\/apisgroup\/2020\/02\/14\/stereoselective-synthesis-of-\u03b1\u03b1\u2032-dihydroxy-\u2032beta-beta-diaryl-amino-acids-by-mannich-like-condensation-of-hydroarylamides\/\" \/>\n<meta property=\"og:site_name\" content=\"APIS group\" \/>\n<meta property=\"article:published_time\" content=\"2020-02-14T13:31:11+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2022-01-21T12:07:54+00:00\" \/>\n<meta property=\"og:image\" content=\"https:\/\/sites.unimi.it\/apisgroup\/wp-content\/uploads\/2020\/02\/ejoc201901325-toc-0001-m.jpg\" \/>\n\t<meta property=\"og:image:width\" content=\"431\" \/>\n\t<meta property=\"og:image:height\" content=\"444\" \/>\n\t<meta property=\"og:image:type\" content=\"image\/jpeg\" \/>\n<meta name=\"author\" content=\"emanuela erba\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<meta name=\"twitter:label1\" content=\"Scritto da\" \/>\n\t<meta name=\"twitter:data1\" content=\"emanuela erba\" \/>\n\t<meta name=\"twitter:label2\" content=\"Tempo di lettura stimato\" \/>\n\t<meta name=\"twitter:data2\" content=\"1 minuto\" \/>\n<script type=\"application\/ld+json\" class=\"yoast-schema-graph\">{\"@context\":\"https:\\\/\\\/schema.org\",\"@graph\":[{\"@type\":\"Article\",\"@id\":\"https:\\\/\\\/sites.unimi.it\\\/apisgroup\\\/2020\\\/02\\\/14\\\/stereoselective-synthesis-of-%ce%b1%ce%b1%e2%80%b2-dihydroxy-%e2%80%b2beta-beta-diaryl-amino-acids-by-mannich-like-condensation-of-hydroarylamides\\\/#article\",\"isPartOf\":{\"@id\":\"https:\\\/\\\/sites.unimi.it\\\/apisgroup\\\/2020\\\/02\\\/14\\\/stereoselective-synthesis-of-%ce%b1%ce%b1%e2%80%b2-dihydroxy-%e2%80%b2beta-beta-diaryl-amino-acids-by-mannich-like-condensation-of-hydroarylamides\\\/\"},\"author\":{\"name\":\"emanuela erba\",\"@id\":\"https:\\\/\\\/sites.unimi.it\\\/apisgroup\\\/#\\\/schema\\\/person\\\/983a9690b88e39642466bb60ddc30c84\"},\"headline\":\"Stereoselective Synthesis of \u03b1,\u03b1\u2032-Dihydroxy-beta, beta\u2032-diaryl-beta-amino Acids by Mannich-Like Condensation of Hydroarylamides\",\"datePublished\":\"2020-02-14T13:31:11+00:00\",\"dateModified\":\"2022-01-21T12:07:54+00:00\",\"mainEntityOfPage\":{\"@id\":\"https:\\\/\\\/sites.unimi.it\\\/apisgroup\\\/2020\\\/02\\\/14\\\/stereoselective-synthesis-of-%ce%b1%ce%b1%e2%80%b2-dihydroxy-%e2%80%b2beta-beta-diaryl-amino-acids-by-mannich-like-condensation-of-hydroarylamides\\\/\"},\"wordCount\":134,\"publisher\":{\"@id\":\"https:\\\/\\\/sites.unimi.it\\\/apisgroup\\\/#organization\"},\"image\":{\"@id\":\"https:\\\/\\\/sites.unimi.it\\\/apisgroup\\\/2020\\\/02\\\/14\\\/stereoselective-synthesis-of-%ce%b1%ce%b1%e2%80%b2-dihydroxy-%e2%80%b2beta-beta-diaryl-amino-acids-by-mannich-like-condensation-of-hydroarylamides\\\/#primaryimage\"},\"thumbnailUrl\":\"https:\\\/\\\/sites.unimi.it\\\/apisgroup\\\/wp-content\\\/uploads\\\/2020\\\/02\\\/ejoc201901325-toc-0001-m.jpg\",\"keywords\":[\"mannich-like\"],\"articleSection\":[\"application\",\"unnatural amino acid\"],\"inLanguage\":\"it-IT\"},{\"@type\":\"WebPage\",\"@id\":\"https:\\\/\\\/sites.unimi.it\\\/apisgroup\\\/2020\\\/02\\\/14\\\/stereoselective-synthesis-of-%ce%b1%ce%b1%e2%80%b2-dihydroxy-%e2%80%b2beta-beta-diaryl-amino-acids-by-mannich-like-condensation-of-hydroarylamides\\\/\",\"url\":\"https:\\\/\\\/sites.unimi.it\\\/apisgroup\\\/2020\\\/02\\\/14\\\/stereoselective-synthesis-of-%ce%b1%ce%b1%e2%80%b2-dihydroxy-%e2%80%b2beta-beta-diaryl-amino-acids-by-mannich-like-condensation-of-hydroarylamides\\\/\",\"name\":\"Stereoselective Synthesis of \u03b1,\u03b1\u2032-Dihydroxy-beta, beta\u2032-diaryl-beta-amino Acids by Mannich-Like Condensation of Hydroarylamides - 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