{"id":3874,"date":"2015-12-02T15:09:29","date_gmt":"2015-12-02T14:09:29","guid":{"rendered":"http:\/\/lewin.ch.pw.edu.pl\/?p=3874"},"modified":"2016-03-10T14:43:01","modified_gmt":"2016-03-10T13:43:01","slug":"me2zn-mediated-catalytic-enantio-and-diastereoselective-addition-of-tosmic-to-ketones","status":"publish","type":"post","link":"https:\/\/lewin.ch.pw.edu.pl\/?p=3874","title":{"rendered":"Enantio- and Diastereoselective Addition of TosMIC to Ketones"},"content":{"rendered":"<div><i>Chemistry, a European Journal<\/i>, <b>2015<\/b>, <i>21<\/i>,18949\u201318952<\/i>.<\/div>\n<div><\/div>\n<div><\/div>\n<p>&nbsp;<\/p>\n<div><strong><span style=\"font-size: 2em;\">Me<sub>2<\/sub>Zn-Mediated Catalytic Enantio- and Diastereoselective Addition of TosMIC to Ketones<\/span><\/strong><\/div>\n<p><strong><br \/>\n<a href=\"?page_id=\"361\">Abdul Raheem Keeri<\/a>,<sup>ab<\/sup> Andrea Gualandi,<sup>a<\/sup> Andrea Mazzanti,<sup>c<\/sup> <a href=\"?page_id=14\">Janusz Lewi\u0144ski<\/a>,<sup>b<\/sup> Pier Giorgio Cozzi<sup>a<\/sup><\/strong><\/p>\n<p><sup>a\u00a0<\/sup>Dipartimento di Chimica \u201cG: Ciamician\u201d, Universit\u00e0 di Bologna, Via Selmi 2, 40126, Bologna, Italy<br \/>\n<sup>b\u00a0<\/sup>Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664, Warsaw, Poland<br \/>\n<sup>c\u00a0<\/sup>Dipartimento di Chimica \u201cToso Montanari\u201d, Universit\u00e0 di Bologna, Viale del Risorgimento 4, 40136, Bologna, Italy<\/p>\n<p><strong>DOI: <\/strong> 10.1002\/chem.201504362.<br \/>\nFirst published online 23 Nov 2015.<\/p>\n<p>The first catalytic asymmetric addition of TosMIC to unactivated ketones is presented. A combination of Me<sub>2<\/sub>Zn and aminoalcohol catalyst promoted the aldol addition\/cyclization reaction to render oxazolines possessing a fully substituted stereocenter with excellent yields (up to 92%), high enantioselectivities (up to 96%), and complete diastereoselectivity. The chiral oxazolines were then used to give, after a straightforward acid hydrolysis, enantioenriched building blocks bearing tertiary alcohol motifs such as hydroxylaldehydes, hydroxylacids, and hydroxylesters without racemization.<\/p>\n<p style=\"text-align: center;\"><img decoding=\"async\" class=\"aligncenter  wp-image-2004\" alt=\"chej2015tosmic\" src=\"http:\/\/lewin.ch.pw.edu.pl\/wp-content\/uploads\/2016\/03\/chej2015tosmic.png\" width=\"630\" \/><\/p>\n<p><a href=\"http:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/chem.201504362\/abstract\" target=\"_blank\">Paper on the Wiley Online Library website<\/a><\/p>\n","protected":false},"excerpt":{"rendered":"<p>Chemistry, a European Journal, 2015, 21,18949\u201318952. &nbsp; Me2Zn-Mediated Catalytic Enantio- and Diastereoselective Addition of TosMIC to Ketones<\/p>\n","protected":false},"author":2,"featured_media":3884,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"inline_featured_image":false,"footnotes":""},"categories":[19],"tags":[],"class_list":["post-3874","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-paper"],"_links":{"self":[{"href":"https:\/\/lewin.ch.pw.edu.pl\/index.php?rest_route=\/wp\/v2\/posts\/3874","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/lewin.ch.pw.edu.pl\/index.php?rest_route=\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/lewin.ch.pw.edu.pl\/index.php?rest_route=\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/lewin.ch.pw.edu.pl\/index.php?rest_route=\/wp\/v2\/users\/2"}],"replies":[{"embeddable":true,"href":"https:\/\/lewin.ch.pw.edu.pl\/index.php?rest_route=%2Fwp%2Fv2%2Fcomments&post=3874"}],"version-history":[{"count":12,"href":"https:\/\/lewin.ch.pw.edu.pl\/index.php?rest_route=\/wp\/v2\/posts\/3874\/revisions"}],"predecessor-version":[{"id":3897,"href":"https:\/\/lewin.ch.pw.edu.pl\/index.php?rest_route=\/wp\/v2\/posts\/3874\/revisions\/3897"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/lewin.ch.pw.edu.pl\/index.php?rest_route=\/wp\/v2\/media\/3884"}],"wp:attachment":[{"href":"https:\/\/lewin.ch.pw.edu.pl\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=3874"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/lewin.ch.pw.edu.pl\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=3874"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/lewin.ch.pw.edu.pl\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=3874"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}