Axially chiral Ni(II) complexes of α‐amino acids: Separation of enantiomers and kinetics of racemization

Zhang Wenzhong; Ekomo Romuald Eto; Roussel Christian; Moriwaki Hiroki; Abe Hidenori; Han Jianlin; Soloshonok Vadim A.

摘要

Abstract > Herein we present design, synthesis, chiral HPLC resolution, and kinetics of racemization of axially chiral Ni(II) complexes of glycine and di‐(benzyl)glycine Schiff bases. We found that while the <fi>ortho</fi> ‐fluoro derivatives are configurationally unstable, the pure enantiomers of corresponding axially chiral <fi>ortho</fi> ‐chloro‐containing complexes can be isolated by preparative HPLC and show exceptional configurational stability (t <sub>1/2</sub> from 4 to 216 centuries) at ambient conditions. Synthetic implications of this discovery for the development of new generation of axially chiral auxiliaries, useful for general asymmetric synthesis of α‐amino acids, are discussed. </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”>摘要</ title> >在此我们呈现设计，合成，手性HPLC分辨率和轴向手性Ni的外向定义的动力学（ii）甘氨酸和二（苄基）甘氨酸席夫基碱的复合物。我们发现，虽然<fi> ortho </ fi> -fluoro衍生物进行配置不稳定，但可以通过制备型HPLC分离相应的轴向手性的纯对映体</ fi> -Chorlo络合物的含量分离，并显示出卓越的配置在环境条件下，稳定性（T <亚> 1/2 </ sub>从4到216个世纪）。讨论了这种发现对新一代轴向手性助剂的发展的综合意义，可用于一般不对称合成α-氨基酸的α-氨基酸。 </ p> </ abstract> </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-16290/'>《Chirality: The pharmacological, biological, and chemical consequences of molecular asymmetry》</a> <b style="margin: 0 2px;">|</b><span>2018年第4期</span><b style="margin: 0 2px;">|</b><span>共11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=Zhang Wenzhong&option=202" target="_blank" rel="nofollow">Zhang Wenzhong;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Ekomo Romuald Eto&option=202" target="_blank" rel="nofollow">Ekomo Romuald Eto;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Roussel Christian&option=202" target="_blank" rel="nofollow">Roussel Christian;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Moriwaki Hiroki&option=202" target="_blank" rel="nofollow">Moriwaki Hiroki;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Abe Hidenori&option=202" target="_blank" rel="nofollow">Abe Hidenori;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Han Jianlin&option=202" target="_blank" rel="nofollow">Han Jianlin;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Soloshonok Vadim A.&option=202" target="_blank" rel="nofollow">Soloshonok Vadim A.;</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>School of Chemistry and Chemical Engineering State Key Laboratory of Coordination ChemistryNanjing UniversityNanjing China;</p> <p>Aix Marseille Univ CNRS Centrale Marseille iSm2Marseille France;</p> <p>Aix Marseille Univ CNRS Centrale Marseille iSm2Marseille France;</p> <p>Hamari Chemicals LtdOsaka Japan;</p> <p>Hamari Chemicals LtdOsaka Japan;</p> <p>School of Chemistry and Chemical Engineering State Key Laboratory of Coordination ChemistryNanjing UniversityNanjing China;</p> <p>Department of Organic Chemistry I Faculty of ChemistryUniversity of the Basque Country UPV/EHUSan Sebastián Spain;</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/4812.html" title="结构化学">结构化学;</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=amino acids&option=203" rel="nofollow">amino acids;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=axial chirality&option=203" rel="nofollow">axial chirality;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=chiral HPLC&option=203" rel="nofollow">chiral HPLC;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=kinetic of racemization&option=203" rel="nofollow">kinetic of racemization;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=rotational energy barriers&option=203" rel="nofollow">rotational energy barriers;</a> </p> <div class="translation"> 机译：氨基酸;轴向手性;手性HPLC;外向性动力化;旋转能量障碍; </div> </li> </ul> </div> </div> <div class="literature cardcommon" id="literaturereference" style="display:none"> <div class="similarity "> <h3 class="all_title" id="enpatent111">引文网络</h3> <div class="referencetab clearfix"> <ul id="referencedaohang"> <li dataid="referenceul">参考文献</li> <li dataid="citationul">引证文献</li> <li dataid="commonreferenceul">共引文献</li> <li dataid="commoncitationul">同被引文献</li> <li dataid="tworeferenceul">二级参考文献</li> <li dataid="twocitationul">二级引证文献</li> </ul> </div> <div class="reference_details" id="referenceList"> <ul id="referenceul"></ul> <ul id="citationul"></ul> <ul id="commonreferenceul"></ul> <ul id="commoncitationul"></ul> <ul id="tworeferenceul"></ul> <ul id="twocitationul"></ul> </div> </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. </b><a class="enjiyixqcontent" href="/journal-foreign-detail/0704022113588.html">Axially chiral Ni(II) complexes of α‐amino acids: Separation of enantiomers and kinetics of racemization</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Zhang Wenzhong&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Zhang Wenzhong,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Ekomo Romuald Eto&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Ekomo Romuald Eto,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Roussel Christian&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Roussel Christian,</a> <a href="/journal-foreign-16290/" target="_blank" rel="nofollow" class="tuijian_authcolor">Chirality: The pharmacological, biological, and chemical consequences of molecular asymmetry .</a> <span>2018</span><span>,第4期</span> </span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: 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href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=罗兴平&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,罗兴平</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=李欣&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,李欣</a> <span> <a href="/journal-cn-10803/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 分析测试学报 </a> </span> <span> . 2005</span><span>,第005期</span> </span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/academic-journal-cn_acta-chimica-sinica_thesis/0201272164964.html">外消旋萘普生酯类在四种纤维素衍生物手性柱上的分离及手性识别机理研究</a> <b>[J]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=邵保海&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 邵保海</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=徐秀珠&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,徐秀珠</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=邹莉&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,邹莉</a> <span> <a href="/journal-cn-53859/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 化学学报 </a> </span> <span> . 2001</span><span>,第011期</span> </span> </div> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/academic-journal-cn_chemical-journal-chinese-universities_thesis/0201231582241.html">三元非对映异构体复合物的直接实验证据及其在对映体手性分离中的作用</a> <b>[J]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=于擎&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 于擎</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=曹洁&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,曹洁</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=张成根&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,张成根</a> <span> <a href="/journal-cn-10958/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 高等学校化学学报 </a> </span> <span> . 2009</span><span>,第005期</span> </span> </div> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/academic-journal-cn_detail_thesis/0201296501898.html">临床病人口服外消旋维拉帕米的对映体药物动力学结合药效学分析</a> <b>[J]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=芮建中&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 芮建中</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=周永刚&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,周永刚</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=凌树森&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,凌树森</a> <span> <a href="/journal-cn-57041/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 中国药科大学学报 </a> </span> <span> . 1998</span><span>,第4期</span> </span> </div> </li> <li> <div> <b>6. </b><a class="enjiyixqcontent" href="/academic-conference-cn_meeting-27196_thesis/020221780270.html">用两种相似多糖类手性固定相拆分阿托品外消旋对映体的比较</a> <b>[C]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=翟宗德&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 翟宗德</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=罗兴平&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,罗兴平</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=李欣&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,李欣</a> <span> <a href="/conference-cn-27196/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 西北地区第三届色谱学术报告会暨甘肃省第八届色谱年会 </a> <span> <span> . 2004</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/020312670499.html">手性萃取分离邻甲扁桃酸和氨基酸对映体动力学研究</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=罗菁菁&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 罗菁菁</a> <span> . 2013</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/0612046730.html">一种柄型金属茂络合物的非手性内消旋形式或外消旋物或其混合物转化成其一种对映体的方法</a> <b>[P]</b> . <span> 中国专利： CN1065867C </span> <span> . 2001.05.16</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06120104386582.html">一种柄型金属茂络合物的非手性内消旋形式或外消旋物或其混合物转化成其一种对映体的方法</a> <b>[P]</b> . <span> 中国专利： CN1190399A </span> <span> . 1998-08-12</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130435048621.html">Resolving racemic 2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole to obtain S-enantiomer, useful as dopamine agonist for treating e.g. Parkinson's disease, comprises conversion to mono-salt with chiral dicarboxylic acid</a> <b>[P]</b> . <span> 外国专利：  ES2264378A1 </span> <span> . 2006-12-16</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：拆分外消旋的2-氨基-6-丙基氨基-4,5,6,7-四氢苯并噻唑以获得S-对映体，可用作多巴胺激动剂，例如用于治疗帕金森氏病，包括用手性二羧酸转化为单盐 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130492866672.html">Method of separation of the enantiomers of amino - racemic acids</a> <b>[P]</b> . <span> 外国专利：  FR1018782A </span> <span> . 1953-01-13</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：氨基外消旋酸对映体的分离方法 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130401875636.html">Process for electrochemical separation of enantiomers of an amino acid from a racemic mixture</a> <b>[P]</b> . <span> 外国专利：  US10793513B2 </span> <span> . 2020-10-06</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：从外消旋混合物中电化学分离氨基酸对映体的方法 </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('0704022113588','4',7,2,1,'',this,24)" class="delivery" prompt="010401" title="通过人工服务将文献原文发送至邮箱" >获取原文</div> <div class="journalsub-pop-up" style="display: none"> <div class="journal-sub"> <h2>期刊订阅</h2> <img src="https://cdn.zhangqiaokeyan.com/img/loginclose.png" alt="关闭" 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