Iron‐Catalysed Reductive Amination of Carbonyl Derivatives with ω‐Amino Fatty Acids to Access Cyclic Amines

Wei Duo; Netkaew Chakkrit; Carré Victor; Darcel Christophe

摘要

Abstract > An efficient method for the reductive amination of carbonyl derivatives with ω‐amino fatty acids catalysed by an iron complex Fe(CO) <sub>4</sub> ( IMes ) [ IMes =1,3‐bis(2,4,6‐trimethylphenyl)imidazol‐2‐ylidene] by means of hydrosilylation was developed. A variety of pyrrolidines, piperidines and azepanes were selectively synthesised in moderate‐to‐excellent yields (36?examples, 47–97?% isolated yield) with a good functional group tolerance. </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> > 一种有效的铁复合物Fe（CO）催化羰基衍生物与ω-氨基脂肪酸的羰基衍生物的减少胺化方法 <sub> 4 </ sub> （ IMES </ I> ）[ IMES </ I> = 1,3-双（2,4,4,6-三甲基苯基）咪唑-2- ylidene]通过氢化硅烷化研制出来。选择性地合成各种吡咯烷，哌啶和叠哌烷，以正至优异的产率（36μm，47-97〜％的分离的产率），具有良好的官能团耐受性。 </ 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-16185/'>《ChemSusChem》</a> <b style="margin: 0 2px;">|</b><span>2019年第13期</span><b style="margin: 0 2px;">|</b><span>共5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=Wei Duo&option=202" target="_blank" rel="nofollow">Wei Duo;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Netkaew Chakkrit&option=202" target="_blank" rel="nofollow">Netkaew Chakkrit;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Carré Victor&option=202" target="_blank" rel="nofollow">Carré Victor;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Darcel Christophe&option=202" target="_blank" rel="nofollow">Darcel Christophe;</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>CNRS ISCR (Institut des Sciences Chimiques de Rennes)Univ. RennesUMR 6226 F-35000 Rennes France;</p> <p>CNRS ISCR (Institut des Sciences Chimiques de Rennes)Univ. RennesUMR 6226 F-35000 Rennes France;</p> <p>CNRS ISCR (Institut des Sciences Chimiques de Rennes)Univ. RennesUMR 6226 F-35000 Rennes France;</p> <p>CNRS ISCR (Institut des Sciences Chimiques de Rennes)Univ. RennesUMR 6226 F-35000 Rennes France;</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/159.html" title="化学">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=cyclic amines&option=203" rel="nofollow">cyclic amines;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=hydrosilylation&option=203" rel="nofollow">hydrosilylation;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=iron catalysis&option=203" rel="nofollow">iron catalysis;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=reductive amination&option=203" rel="nofollow">reductive amination;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=ω-amino fatty acids&option=203" rel="nofollow">ω-amino fatty acids;</a> </p> <div class="translation"> 机译：循环胺;乳液;铁催化;还原胺化;ω-氨基脂肪酸; </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. </b><a class="enjiyixqcontent" href="/journal-foreign-detail/0704022092997.html">Iron‐Catalysed Reductive Amination of Carbonyl Derivatives with ω‐Amino Fatty Acids to Access Cyclic 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href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=黎星术&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,黎星术</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=陈新滋&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,陈新滋</a> <span> <a href="/conference-cn-27452/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 第七届全国青年药学工作者最新科研成果交流会 </a> <span> <span> . 2004</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/020314316693.html">L-α-氨基酸衍生物的合成与生物活性测定：（Ⅰ）：N-（5-邻氯苯基-2-呋喃甲酰氨基硫羰基）-L-α-氨基酸乙酯的合成与生物活性测定;（Ⅱ）：N-（5-邻氯苯基-2-呋喃甲酰基）甘氨酰胺衍生物的合成与生物活性测定;（Ⅲ）：N-（5-邻氯苯基-2-呋喃甲酰基）甘氨酰肼衍生物的合成与生物活性测定</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=王庆东&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 王庆东</a> <span> . 2007</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/06120102744411.html">N-取代的氨基苯并环庚烯、氨基四氢化萘、氨基茚满和苯烷基胺衍生物、包含所述衍生物的药物组合物及其在治疗中的用途</a> <b>[P]</b> . <span> 中国专利： CN104011028A </span> <span> . 2014-08-27</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/061204433534.html">催化氧化氨基烯烃胺羰基化制备五并七元高哌嗪酮衍生物的方法</a> <b>[P]</b> . <span> 中国专利： CN112062769B </span> <span> . 2021.06.01</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130454271412.html">REDUCTIVE AMINATION OF AN AMINO ACID OR AN AMINO ACID DERIVATIVE WITH AN ALPHA-KETO ACID OR AN ALPHA-KETO ACID DERIVATIVE</a> <b>[P]</b> . <span> 外国专利：  SG48736A1 </span> <span> . 1998-05-18</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α-酮酸或α-酮酸衍生物还原胺化氨基酸或氨基酸衍生物 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130455983009.html">Reductive amination of an amino acid or of an amino acid derivative with an alpha-keto acid or an alpha-keto acid derivative</a> <b>[P]</b> . <span> 外国专利：  IE73437B1 </span> <span> . 1997-06-04</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α-酮酸或α-酮酸衍生物还原氨基酸或氨基酸衍生物 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130457346282.html">Reductive amination of an amino acid or amino acid derivative with an alpha-ketoacid or a derivative of an alpha-ketoacid.</a> <b>[P]</b> . <span> 外国专利：  ES2052492T3 </span> <span> . 1996-07-16</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：氨基酸或氨基酸衍生物与α-酮酸或α-酮酸衍生物的还原胺化。 </span> </p> </li> 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