{"id":2640,"date":"2010-03-03T14:26:42","date_gmt":"2010-03-03T12:26:42","guid":{"rendered":"https:\/\/ospt.osi.lv\/?p=2640"},"modified":"2022-01-11T12:12:36","modified_gmt":"2022-01-11T10:12:36","slug":"asymmetric-synthesis-of-13-diamines","status":"publish","type":"post","link":"https:\/\/ospt.osi.lv\/asymmetric-synthesis-of-13-diamines\/","title":{"rendered":"5. Asymmetric Synthesis of 1,3-Diamines by Diastereoselective Reduction of Enantiopure N\u2013tert-Butanesulfinylketimines: Unusual Directing Effects of the ortho-Substituent"},"content":{"rendered":"<p>Martjuga, M.; Shabashov, D.; Belyakov, S.; Liepinsh, E.; Suna, E. <em>J. Org. Chem. <\/em><strong>2010<\/strong>, <em>75<\/em>, 2375-2368.<br \/>\nDOI: <a href=\"http:\/\/pubs.acs.org\/doi\/abs\/10.1021\/jo100173f\" target=\"_blank\" rel=\"noopener\">10.1021\/jo100173f<\/a><\/p>\n<h4><!--more-->Abstract<\/h4>\n<p>Chiral, nonracemic 1,3-diamines were prepared in a highly diastereoselective reduction of diaryl <i>N<\/i>&#8211;<i>tert<\/i>-butanesulfinylketimines. Correlation between facial selectivity of the reduction and <i>E<\/i> or <i>Z<\/i> geometry of the starting ketimines suggests involvement of a cyclic transition state for the reduction. The <i>ortho<\/i>-substituent controls the geometry of <i>N<\/i>&#8211;<i>tert<\/i>-butanesulfinylketimines in the solid state and provides additional stabilization of the cyclic transition state.<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Martjuga, M.; Shabashov, D.; Belyakov, S.; Liepinsh, E.; Suna, E. J. Org. Chem. 2010, 75, 2375-2368. DOI: 10.1021\/jo100173f<\/p>\n","protected":false},"author":1,"featured_media":2641,"comment_status":"closed","ping_status":"open","sticky":false,"template":"","format":"image","meta":{"_exactmetrics_skip_tracking":false,"_exactmetrics_sitenote_active":false,"_exactmetrics_sitenote_note":"","_exactmetrics_sitenote_category":0,"footnotes":""},"categories":[44,16],"tags":[],"aioseo_notices":[],"_links":{"self":[{"href":"https:\/\/ospt.osi.lv\/wp-json\/wp\/v2\/posts\/2640"}],"collection":[{"href":"https:\/\/ospt.osi.lv\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/ospt.osi.lv\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/ospt.osi.lv\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/ospt.osi.lv\/wp-json\/wp\/v2\/comments?post=2640"}],"version-history":[{"count":1,"href":"https:\/\/ospt.osi.lv\/wp-json\/wp\/v2\/posts\/2640\/revisions"}],"predecessor-version":[{"id":3978,"href":"https:\/\/ospt.osi.lv\/wp-json\/wp\/v2\/posts\/2640\/revisions\/3978"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/ospt.osi.lv\/wp-json\/wp\/v2\/media\/2641"}],"wp:attachment":[{"href":"https:\/\/ospt.osi.lv\/wp-json\/wp\/v2\/media?parent=2640"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/ospt.osi.lv\/wp-json\/wp\/v2\/categories?post=2640"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/ospt.osi.lv\/wp-json\/wp\/v2\/tags?post=2640"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}