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A Mechanistic Study of the Stereochemical Outcomes of Rhodium‐Catalysed Styrene Aziridinations

机译：铑催化苯乙烯氮杂化的立体化学结果的机制研究

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Abstract > The stereoselective, rhodium‐catalysed aziridination of styrene derivatives with a chiral N ‐mesyloxycarbamate was found to be highly substrate dependent. A density functional theory (DFT) study is herein reported to elucidate the stereochemical outcome of the aziridination process. Rhodium acetate was initially used as a model catalyst, followed by computational studies conducted with Rh <sub>2</sub> [( S )‐nttl] <sub>4</sub> . Both singlet and triplet rhodium nitrene species were identified as intermediates affording concomitant concerted and radical pathways. In the latter case, the radical intermediate appears to undergo a direct ring closure via a minimum energy crossing point (MECP) between the triplet and closed‐shell singlet surfaces. Exceptionally for the m ‐Br‐styrene aziridination, an alternative radical pathway with a carbon‐carbon bond rotation was observed, accounting for the observed 74:26 mixture of diastereomers. The computational analysis also suggests little control of the metal nitrene conformation with Rh <sub>2</sub> (OAc) <sub>4</sub> with the chiral N ‐mesyloxycarbamate: two conformers were located affording two diastereomers of the aziridine and correlating our experimental results. On the other hand, only one conformer was found for the nitrene generated from the chiral N ‐mesyloxycarbamate and Rh <sub>2</sub> [( S )‐nttl] <sub>4</sub> . The so‐called “all‐up” conformer of Rh <sub>2</sub> [( S )‐nttl] <sub>4</sub> was not only the most stable metal nitrene species, but also afforded the lowest energy transition state. The calculated dr for p ‐Br‐styrene aziridination agrees with the observed experimental result. The combination of experimental and computational results offers a detailed mechanistic picture, providing insights for further catalyst development to enhance reactivity and selectivity. > <blockFixed type="graphic"> <mediaResourceGroup> <mediaResource alt="image" href="urn:x-wiley:16154150:media:adsc201901184:adsc201901184-toc-0001"/> </mediaResourceGroup> </blockFixed> </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> > 具有手性的立体选择性，铑催化苯乙烯衍生物的αzirination n </ i> 发现 - 羟基氨基甲酸酯是高度基底依赖性的。本文据报道，密度泛函理论（DFT）研究阐明了亚氮化过程的立体化学结果。醋酸铑最初用作模型催化剂，然后用RH进行的计算研究 <sub> 2 </ sub> [（ s </ i> ）-nttl] <sub> 4 </ sub> 。单态和三联铑硝酸铑物种被鉴定为提供伴随的齐全和自由基途径的中间体。在后一种情况下，自由基中间体似乎通过三联和闭合壳单次表面之间的最小能量交叉点（MECP）进行直圈闭合。特别适用于 m </ i> -BR-苯乙烯叠氮化，观察到具有碳碳键旋转的替代自由基途径，占观察到的74:26的非对映异构体的混合物。计算分析还表明，对rh的金属硝化族构象的控制很小 <sub> 2 </ sub> （OAC） <sub> 4 </ sub> 用手段 n </ i> - 镁氧基氨基甲酸酯：两种塑形剂位于氮啶的两个非对映异构体，并关联我们的实验结果。另一方面，发现从手性产生的硝化乙烯中只发现一个符合子 n </ i> -mesyloxycarbamate和Rh. <sub> 2 </ sub> [（ s </ i> ）-nttl] <sub> 4 </ sub> 。 RH的所谓“全升”符合子 <sub> 2 </ sub> [（ s </ i> ）-nttl] <sub> 4 </ sub> 不仅是最稳定的金属硝酸盐物质，还提供了最低能量过渡状态。计算的博士 p </ i> -BR-苯乙烯叠氮化同意观察到的实验结果。实验和计算结果的组合提供了一个详细的机械图，提供了进一步催化剂开发的见解，以提高反应性和选择性。 </ p> > <blockfixed type =“图形”> <mediaresourcegroup> <MediareSource Alt =“图像”Href =“URN：X-Wiley：16154150：介质：ADSC201901184：ADSC201901184-TOC-0001”/> </ mediaresourcegroup> </ blockfixed> </ 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-19407/'>《Advanced synthesis & catalysis》</a> <b style="margin: 0 2px;">|</b><span>2020年第2期</span><b style="margin: 0 2px;">|</b><span>共14页</span> </div> </li> <li> <div class="author"> <span class="lefttit">作者</span> <p id="fAuthorthree" class="threelineshidden zhankaihshouqi"> </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"> </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/238.html" title="化学工业">化学工业;</a><a href="https://www.zhangqiaokeyan.com/clc/1186.html" title="物理化学（理论化学）、化学物理学">物理化学（理论化学）、化学物理学;</a><a href="https://www.zhangqiaokeyan.com/clc/7777.html" title="化学反应过程">化学反应过程;</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=Nitrogen&option=203" rel="nofollow">Nitrogen;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Heterocycle&option=203" rel="nofollow">Heterocycle;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Asymmetric&option=203" rel="nofollow">Asymmetric;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Catalyst&option=203" rel="nofollow">Catalyst;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Two-state process&option=203" rel="nofollow">Two-state process;</a> </p> <div class="translation"> 机译：氮气;杂环;不对称;催化剂;双态过程; 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