The Importance of 1,5‐Oxygen???Chalcogen Interactions in Enantioselective Isochalcogenourea Catalysis

Young Claire M.; Elmi Alex; Pascoe Dominic J.; Morris Rylie K.; McLaughlin Calum; Woods Andrew M.; Frost Aileen B.; Houpliere Alix; Ling Kenneth B.; Smith Terry K.; Slawin Alexandra M. Z.; Willoughby Patrick H.; Cockroft Scott L.; Smith Andrew D.

摘要

Abstract > The importance of 1,5‐O???chalcogen (Ch) interactions in isochalcogenourea catalysis (Ch=O, S, Se) is investigated. Conformational analyses of N ‐acyl isochalcogenouronium species and comparison with kinetic data demonstrate the significance of 1,5‐O???Ch interactions in enantioselective catalysis. Importantly, the selenium analogue demonstrates enhanced rate and selectivity profiles across a range of reaction processes including nitronate conjugate addition and formal [4+2] cycloadditions. A gram‐scale synthesis of the most active selenium analogue was developed using a previously unreported seleno‐Hugerschoff reaction, allowing the challenging kinetic resolutions of tertiary alcohols to be performed at 500?ppm catalyst loading. Density functional theory (DFT) and natural bond orbital (NBO) calculations support the role of orbital delocalization (occurring by intramolecular chalcogen bonding) in determining the conformation, equilibrium population, and reactivity of N‐acylated intermediates. </abstract> </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> <div class="translation abstracttxt"> <span class="zhankaihshouqi fivelineshidden" id="abstract"> <span>机译：</span><Abstract Type =“Main”XML：Lang =“en”> <标题类型=“main”>抽象</ title> > 研究了1,5-O ???的重要性（ChalogogoRea催化催化剂（Ch = O，S，Se）的重要性。构象分析 n </ i> - 羰基遗传学物种和与动力学数据的比较证明了1,5-O ??? Ch相互作用的重要性。重要的是，硒模拟显示出在一系列反应过程中增强的速率和选择性曲线，包括氮酸盐缀合物添加和正式的[4 + 2]环加成。使用先前未报告的Seleno-Hugerschoff反应开发了最活性硒模块的革兰氏型合成，允许在500μlPPM催化剂负载下进行初步的叔醇的动力学分辨率。密度函数理论（DFT）和天然键（NBO）计算支持轨道删除（通过分子内降钙素键）的作用确定N-酰化中间体的构象，平衡群体和反应性。 </ p> </摘要> </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> </div> <div class="record"> <h2 class="all_title" id="enpatent33" >著录项</h2> <ul> <li> <span class="lefttit">来源</span> <div style="width: 86%;vertical-align: text-top;display: inline-block;"> <a href='/journal-foreign-19011/'>《Angewandte Chemie》</a> <b style="margin: 0 2px;">|</b><span>2020年第9期</span><b style="margin: 0 2px;">|</b><span>共6页</span> </div> </li> <li> <div class="author"> <span class="lefttit">作者</span> <p id="fAuthorthree" class="threelineshidden zhankaihshouqi"> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Young Claire M.&option=202" target="_blank" rel="nofollow">Young Claire M.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Elmi Alex&option=202" target="_blank" rel="nofollow">Elmi Alex;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Pascoe Dominic J.&option=202" target="_blank" rel="nofollow">Pascoe Dominic J.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Morris Rylie K.&option=202" target="_blank" rel="nofollow">Morris Rylie K.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=McLaughlin Calum&option=202" target="_blank" rel="nofollow">McLaughlin Calum;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Woods Andrew M.&option=202" target="_blank" rel="nofollow">Woods Andrew M.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Frost Aileen B.&option=202" target="_blank" rel="nofollow">Frost Aileen B.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Houpliere Alix&option=202" target="_blank" rel="nofollow">Houpliere Alix;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Ling Kenneth B.&option=202" target="_blank" rel="nofollow">Ling Kenneth B.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Smith Terry K.&option=202" target="_blank" rel="nofollow">Smith Terry K.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Slawin Alexandra M. Z.&option=202" target="_blank" rel="nofollow">Slawin Alexandra M. Z.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Willoughby Patrick H.&option=202" target="_blank" rel="nofollow">Willoughby Patrick H.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Cockroft Scott L.&option=202" target="_blank" rel="nofollow">Cockroft Scott L.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Smith Andrew D.&option=202" target="_blank" rel="nofollow">Smith Andrew D.;</a> </p> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zkzz" style="display: none;">展开▼</span> </div> </li> <li> <div style="display: flex;"> <span class="lefttit">作者单位</span> <div style="position: relative;margin-left: 3px;max-width: 639px;"> <div class="threelineshidden zhankaihshouqi" id="fOrgthree"> <p>EaStCHEM School of ChemistryUniversity of St AndrewsNorth Haugh St Andrews KY16 9ST UK;</p> <p>EaStCHEM School of ChemistryUniversity of EdinburghDavid Brewster Road Edinburgh EH9 3FJ UK;</p> <p>EaStCHEM School of ChemistryUniversity of EdinburghDavid Brewster Road Edinburgh EH9 3FJ UK;</p> <p>Chemistry DepartmentRipon College300 W. Seward St. Ripon WI 54971 USA;</p> <p>EaStCHEM School of ChemistryUniversity of St AndrewsNorth Haugh St Andrews KY16 9ST UK;</p> <p>EaStCHEM School of ChemistryUniversity of St AndrewsNorth Haugh St Andrews KY16 9ST UK;</p> <p>EaStCHEM School of ChemistryUniversity of St AndrewsNorth Haugh St Andrews KY16 9ST UK;</p> <p>EaStCHEM School of ChemistryUniversity of St AndrewsNorth Haugh St Andrews KY16 9ST UK;</p> <p>Jealott's Hill International Research CentreSyngentaBracknell Berkshire RG42 6EY UK;</p> <p>EaStCHEM School of ChemistryUniversity of St AndrewsNorth Haugh St Andrews KY16 9ST UK;</p> <p>EaStCHEM School of ChemistryUniversity of St AndrewsNorth Haugh St Andrews KY16 9ST UK;</p> <p>Chemistry DepartmentRipon College300 W. Seward St. Ripon WI 54971 USA;</p> <p>EaStCHEM School of ChemistryUniversity of EdinburghDavid Brewster Road Edinburgh EH9 3FJ UK;</p> <p>EaStCHEM School of ChemistryUniversity of St AndrewsNorth Haugh St Andrews KY16 9ST UK;</p> </div> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zhdw" style="display: none;">展开▼</span> </div> </div> </li> <li > <span class="lefttit">收录信息</span> <span style="width: 86%;vertical-align: text-top;display: inline-block;"></span> </li> <li> <span class="lefttit">原文格式</span> <span>PDF</span> </li> <li> <span class="lefttit">正文语种</span> <span>eng</span> </li> <li> <span class="lefttit">中图分类</span> <span><a href="https://www.zhangqiaokeyan.com/clc/1188.html" title="应用化学">应用化学;</a></span> </li> <li class="antistop"> <span class="lefttit">关键词</span> <p style="width: 86%;vertical-align: text-top;"> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=asymmetric catalysis&option=203" rel="nofollow">asymmetric catalysis;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=chalcogen bonding&option=203" rel="nofollow">chalcogen bonding;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=isothioureas&option=203" rel="nofollow">isothioureas;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=isoselenoureas&option=203" rel="nofollow">isoselenoureas;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=organocatalysis&option=203" rel="nofollow">organocatalysis;</a> </p> <div class="translation"> 机译：不对称催化;硫醇结合;异毛胃;isoselenoureas;有机成分分析; </div> </li> </ul> </div> </div> <div class="literature cardcommon"> <div class="similarity "> <h3 class="all_title" id="enpatent66">相似文献</h3> <div class="similaritytab clearfix"> <ul> <li class="active" >外文文献</li> <li >中文文献</li> <li >专利</li> </ul> </div> <div class="similarity_details"> <ul > <li> <div> <b>1. 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href="/academic-conference-cn_meeting-31725_thesis/02022426739.html">硫鸟嘌呤与核酸相互作用的室温磷光研究</a> <b>[C]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=袁雯&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 袁雯</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=董川&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,董川</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=晋卫军&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,晋卫军</a> <span> <a href="/conference-cn-31725/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 第十一届有机分析和生物分析学术研讨会 </a> <span> <span> . 2001</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/020311848311.html">双咔啉手性催化剂的合成及其在对映选择性反应中的应用</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=王杰&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 王杰</a> <span> . 2019</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/061204611429.html">一种核酸复合体中核酸区段相互作用的分析方法</a> <b>[P]</b> . <span> 中国专利： CN108300767B </span> <span> . 2021.08.20</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06120110790488.html">一种核酸复合体中核酸区段相互作用的分析方法</a> <b>[P]</b> . <span> 中国专利： CN108300767A </span> <span> . 2018-07-20</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130451522732.html">Isolated spinach ribulose-1,5-bisphosphate carboxylase/oxygenase large subunit .sup. 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href="/patent-detail/06130410115121.html">TRANSITION METAL COMPLEXES FOR ENANTIOSELECTIVE CATALYSIS OF CARBON-CARBON, CARBON-HETEROATOM, AND CARBON-HYDROGEN BOND FORMING REACTIONS</a> <b>[P]</b> . <span> 外国专利：  US2017044198A1 </span> <span> . 2017-02-16</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：用于碳-碳，碳-杂原子和碳-氢键形成反应的对映选择性催化的过渡金属配合物 </span> </p> </li> </ul> </div> </div> </div> <div class="theme cardcommon" style="overflow: auto;display:none"> <h3 class="all_title" id="enpatent55">相关主题</h3> <ul id="subject"> </ul> </div> </div> </div> </div> <div class="right rightcon"> <div class="details_img cardcommon clearfix" style="margin-bottom: 10px;display:none;" > </div> </div> </div> <div id="thesis_get_original1" class="downloadBth" style="bottom: 19px;z-index: 999;" onclick="ywcd('0704028162195','4',7,2,1,'',this,24)" class="delivery" prompt="010401" 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