{"id":2017,"date":"2010-05-26T11:34:50","date_gmt":"2010-05-26T10:34:50","guid":{"rendered":"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=2017"},"modified":"2011-07-07T06:06:23","modified_gmt":"2011-07-07T06:06:23","slug":"anatomy-of-an-asymmetric-reaction-the-strecker-synthesis-part-2","status":"publish","type":"post","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=2017","title":{"rendered":"Anatomy of an asymmetric reaction. The Strecker synthesis, part 2."},"content":{"rendered":"<div class=\"kcite-section\" kcite-section-id=\"2017\">\n<p>In the first part of the post on this topic, I described how an asymmetric sulfoxide could be prepared as a pure enantiomer using a chiral oxygen transfer reagent.  In the second part, we now need to deliver a different group, cyano, to a specific face of the previously prepared sulfoxide-imine.  The sulfoxide is now acting as a chiral auxilliary, and helps direct the delivery of the cyanide group to specifically one face of the imine rather than the other.   After removal of the aluminum carrier for the cyano group and hydrolysis of the cyano group to a carboxylic acid group, we end up with an enantiomerically pure amino acid.<\/p>\n<p><div id=\"attachment_2018\" style=\"width: 410px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" aria-describedby=\"caption-attachment-2018\" class=\"size-full wp-image-2018\" title=\"strecker4\" onclick=\"jmolInitialize('..\/Jmol\/');jmolSetAppletColor('green');jmolApplet([600,600],'load wp-content\/uploads\/2010\/05\/TS2-SS.log.gz;frame 3;set measurementUnits Angstroms;delay 5;vectors on;vectors 4;vectors scale 5.0; color vectors green; vibration 15;animation mode loop;connect (atomno=21) (atomno=4) PARTIAL;measure 3 4 21;set fontscaling TRUE;font label 36;select atomno=4;label %A S;select atomno=2;label %A S;measure 18 28;measure 23 29;');\" src=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2010\/05\/strecker4.jpg\" alt=\"\" width=\"400\" height=\"116\" \/><p id=\"caption-attachment-2018\" class=\"wp-caption-text\">The Strecker synthsis: asymmetric delivery of cyanide anion. Click for 3D model of transition state<\/p><\/div>Two transition states can be computed  (\u03c9B97XD\/6-311G(d,p)\/SCRF[dichloromethane], see DOI <a href=\"http:\/\/hdl.handle.net\/10042\/to-4927\">10042\/to-4927<\/a>) and the S,S(S) diastereomer is found to be \u00a01.35 kcal\/mol lower in total free energy than the R,S(S) isomer. This agrees with the observed specificity. Again, a reason for the specificity needs identifying, and again we use \u00a0AIM.<\/p>\n<p><div id=\"attachment_2027\" style=\"width: 410px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" aria-describedby=\"caption-attachment-2027\" class=\"size-full wp-image-2027\" title=\"TS2-SS\" onclick=\"jmolInitialize('..\/Jmol\/');jmolSetAppletColor('yellow');jmolApplet([600,600],'load wp-content\/uploads\/2010\/05\/TS2-SS-aim.mol;connect (atomno=21) (atomno=4) PARTIAL;connect (atomno=54) (atomno=4) NONE;connect (atomno=54) (atomno=21) NONE;measure 3 4 21;set fontscaling TRUE;font label 24;select atomno=62;label %A \u03c1(r)=0.012;');\" src=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2010\/05\/TS2-SS.jpg\" alt=\"\" width=\"400\" height=\"545\" \/><p id=\"caption-attachment-2027\" class=\"wp-caption-text\">AIM analysis for the asymmetric delivery of cyanide to an imine, S,S(S) form.<\/p><\/div>In the favoured diastereomer, a BCP or bond-critical-point (green arrow above) can be found connecting a hydrogen from an aryl group to the  oxygen of the Al-OMe group \u00a0<em>via<\/em> a weak hydrogen bond (H&#8230;O distance  2.25\u00c5). In the disfavoured form,  this interaction vanishes, and is instead replaced by a repulsive  close N=CH&#8230;C-aryl contact of 2.49\u00c5\u00a0(for which there is no \u00a0BCP, red arrow below).<\/p>\n<div id=\"attachment_2037\" style=\"width: 384px\" class=\"wp-caption aligncenter\"><a href=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2010\/05\/TS2-RS.jpg\"><img loading=\"lazy\" decoding=\"async\" aria-describedby=\"caption-attachment-2037\" class=\"size-full wp-image-2037\" title=\"TS2-RS\" src=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2010\/05\/TS2-RS.jpg\" alt=\"\" width=\"374\" height=\"354\" \/><\/a><p id=\"caption-attachment-2037\" class=\"wp-caption-text\">Disfavoured transition state. R,S(S) form.<\/p><\/div>\n<p>The take home message from these two posts is that quite unusual interactions may often be responsible for asymmetric induction in a stereospecific reaction, and that helpful clues to these interactions may well be derived from an AIM analysis.  Indeed, anyone doing stereospecific synthesis in the lab should be familiar with these methods! You have to be a jack-of-all-trades nowadays to keep up!<\/p>\n<!-- kcite active, but no citations found -->\n<\/div> <!-- kcite-section 2017 -->","protected":false},"excerpt":{"rendered":"<p>In the first part of the post on this topic, I described how an asymmetric sulfoxide could be prepared as a pure enantiomer using a chiral oxygen transfer reagent. In the second part, we now need to deliver a different group, cyano, to a specific face of the previously prepared sulfoxide-imine. The sulfoxide is now [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"jetpack_post_was_ever_published":false,"_jetpack_newsletter_access":"","_jetpack_dont_email_post_to_subs":false,"_jetpack_newsletter_tier_id":0,"_jetpack_memberships_contains_paywalled_content":false,"_jetpack_memberships_contains_paid_content":false,"activitypub_content_warning":"","activitypub_content_visibility":"","activitypub_max_image_attachments":5,"activitypub_interaction_policy_quote":"anyone","activitypub_status":"","footnotes":"","jetpack_publicize_message":"","jetpack_publicize_feature_enabled":true,"jetpack_social_post_already_shared":false,"jetpack_social_options":{"image_generator_settings":{"template":"highway","default_image_id":0,"font":"","enabled":false},"version":2}},"categories":[4],"tags":[234,233,575,235,40,2648],"ppma_author":[2661],"class_list":["post-2017","post","type-post","status-publish","format-standard","hentry","category-interesting-chemistry","tag-aluminum-carrier","tag-carboxylic-acid","tag-chiroptical","tag-cyano","tag-free-energy","tag-interesting-chemistry"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.5 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Anatomy of an asymmetric reaction. The Strecker synthesis, part 2. - Henry Rzepa&#039;s Blog<\/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.ch.ic.ac.uk\/rzepa\/blog\/?p=2017\" \/>\n<meta property=\"og:locale\" content=\"en_GB\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Anatomy of an asymmetric reaction. The Strecker synthesis, part 2. - Henry Rzepa&#039;s Blog\" \/>\n<meta property=\"og:description\" content=\"In the first part of the post on this topic, I described how an asymmetric sulfoxide could be prepared as a pure enantiomer using a chiral oxygen transfer reagent. In the second part, we now need to deliver a different group, cyano, to a specific face of the previously prepared sulfoxide-imine. The sulfoxide is now [&hellip;]\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=2017\" \/>\n<meta property=\"og:site_name\" content=\"Henry Rzepa&#039;s Blog\" \/>\n<meta property=\"article:published_time\" content=\"2010-05-26T10:34:50+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2011-07-07T06:06:23+00:00\" \/>\n<meta property=\"og:image\" content=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2010\/05\/strecker4.jpg\" \/>\n<meta name=\"author\" content=\"Henry Rzepa\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<meta name=\"twitter:label1\" content=\"Written by\" \/>\n\t<meta name=\"twitter:data1\" content=\"Henry Rzepa\" \/>\n\t<meta name=\"twitter:label2\" content=\"Estimated reading time\" \/>\n\t<meta name=\"twitter:data2\" content=\"2 minutes\" \/>\n<!-- \/ Yoast SEO plugin. -->","yoast_head_json":{"title":"Anatomy of an asymmetric reaction. 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The sulfoxide is now [&hellip;]","og_url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=2017","og_site_name":"Henry Rzepa&#039;s Blog","article_published_time":"2010-05-26T10:34:50+00:00","article_modified_time":"2011-07-07T06:06:23+00:00","og_image":[{"url":"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2010\/05\/strecker4.jpg","type":"","width":"","height":""}],"author":"Henry Rzepa","twitter_card":"summary_large_image","twitter_misc":{"Written by":"Henry Rzepa","Estimated reading time":"2 minutes"},"schema":{"@context":"https:\/\/schema.org","@graph":[{"@type":"Article","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=2017#article","isPartOf":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=2017"},"author":{"name":"Henry Rzepa","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/#\/schema\/person\/2b40f7b9c872a4dc1547e040a11b6281"},"headline":"Anatomy of an asymmetric reaction. 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Most would agree it reached its most famous achievement with Woodward's synthesis of quinine (DOI:\u2026","rel":"","context":"In &quot;Interesting chemistry&quot;","block_context":{"text":"Interesting chemistry","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=4"},"img":{"alt_text":"","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2010\/05\/strecker0.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":745,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=745","url_meta":{"origin":2017,"position":1},"title":"Spotting the unexpected: Anomeric effects","author":"Henry Rzepa","date":"September 18, 2009","format":false,"excerpt":"Chemistry can be very focussed nowadays. This especially applies to target-driven synthesis, where the objective is to make a specified molecule, in perhaps as an original manner as possible. A welcome, but not always essential aspect of such syntheses is the discovery of new chemistry. In this blog, I will\u2026","rel":"","context":"In &quot;Chemical IT&quot;","block_context":{"text":"Chemical IT","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=2"},"img":{"alt_text":"A cyano-substituted cis decalin","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2009\/09\/anomeric-cn.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":7678,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=7678","url_meta":{"origin":2017,"position":2},"title":"Frozen Semibullvalene: a holy grail (and a bis-homoaromatic molecule).","author":"Henry Rzepa","date":"September 15, 2012","format":false,"excerpt":"Semibullvalene is an unsettling molecule. Whilst it has a classical structure describable by a combination of Lewis-style two electron and four electron bonds, its NMR behaviour reveals it to be highly fluxional. This means that even at low temperatures, the position of these two-electron bonds rapidly shifts in the equilibrium\u2026","rel":"","context":"In &quot;Interesting chemistry&quot;","block_context":{"text":"Interesting chemistry","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=4"},"img":{"alt_text":"","src":"https:\/\/i0.wp.com\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2012\/09\/CAZFUE1.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":16902,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=16902","url_meta":{"origin":2017,"position":3},"title":"\u03c3 or \u03c0 nucleophilic reactivity of imines? A mechanistic twist emerges.","author":"Henry Rzepa","date":"September 28, 2016","format":false,"excerpt":"The story so far. Imines react with a peracid to form either a nitrone (\u03c3-nucleophile) or an oxaziridine (\u03c0-nucleophile). The balance between the two is on an experimental\u00a0knife-edge, being strongly influenced by substituents on the imine. Modelling these reactions using the \"normal\" mechanism for peracid oxidation did not reproduce this\u2026","rel":"","context":"In &quot;reaction mechanism&quot;","block_context":{"text":"reaction mechanism","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=1086"},"img":{"alt_text":"6ts-irc1","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2016\/09\/6TS-IRC1.gif?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":18091,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=18091","url_meta":{"origin":2017,"position":4},"title":"The conformation of carboxylic acids revealed.","author":"Henry Rzepa","date":"April 11, 2017","format":false,"excerpt":"Following my conformational exploration of enols, here is one about a much more common molecule, a carboxylic acid. The components of the search are shown as four queries below, which will be combined in various Boolean senses (DOI:\u00a010.14469\/hpc\/2462). Query one defines the carboxylic acid, with 3-coordinate carbon specified at the\u2026","rel":"","context":"In &quot;crystal_structure_mining&quot;","block_context":{"text":"crystal_structure_mining","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=1745"},"img":{"alt_text":"","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2017\/04\/051-1024x676.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":6044,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=6044","url_meta":{"origin":2017,"position":5},"title":"Secrets of a university tutor: tetrahedral intermediates.","author":"Henry Rzepa","date":"January 8, 2012","format":false,"excerpt":"The tetrahedral intermediate is one of those iconic species on which the foundation of reaction mechanism in organic chemistry is built. 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