Oxa‐Michael Addition to α,β‐Unsaturated Nitriles: An Expedient Route to γ‐Amino Alcohols and Derivatives

摘要

Abstract > Water addition to α,β‐unsaturated nitriles would give facile access to the β‐hydroxy‐nitriles, which in turn can be hydrogenated to the γ‐amino alcohols. We have previously shown that alcohols readily add in 1,4‐fashion to these substrates using Milstein's Ru(PNN) pincer complex as catalyst. However, attempted water addition to α,β‐unsaturated nitriles gave the 3‐hydroxynitriles in mediocre yields. On the other hand, addition of benzyl alcohol proceeded in excellent yields for a variety of β‐substituted unsaturated nitriles. Subsequent treatment of the benzyl alcohol addition products with TMSCl/FeCl <sub>3</sub> resulted in the formation of 3‐hydroxy‐alkylnitriles. The 3‐benzyloxy‐alkylnitriles obtained from oxa‐Michael addition also could be hydrogenated directly in the presence of acid to give the amino alcohols as their HCl salts in excellent yields. Hydrogenation under neutral conditions gave a mixture of the secondary and tertiary amines. Hydrogenation in the presence of base and Boc‐anhydride gave the orthogonally bis‐protected amino alcohols, in which the benzyl ether can subsequently be cleaved to yield Boc‐protected amino alcohols. Thus, a variety of molecular scaffolds with a 1,3‐relationship between O ‐ and N ‐functional group is accessible starting from oxa‐Michael addition of benzyl alcohol to α,β‐unsaturated nitriles. </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> > 除了α，β-不饱和腈的水分将适用于β-羟基腈的容易进入，这又可以氢化到γ-氨基醇中。我们之前已经表明，使用Milstein的Ru（PNN）钳子复合物作为催化剂，醇容易加入1,4时的底物。然而，尝试的水除α，β-不饱和腈中的水加入3-羟基丙烯。另一方面，添加苄醇以优异的产率为各种β-取代的不饱和腈进行。随后用TMSCl / FECL处理苄醇加成产物 <sub> 3 </ sub> 导致形成3-羟基 - 烷基腈。由Oxa-Michael添加的3-苄氧基 - 烷基腈也可以在酸存在下直接氢化，得到氨基醇，作为其HCl盐以优异的产率。中性条件下的氢化得到了二级和叔胺的混合物。在碱基和Boc-酐存在下氢化，得到正交的双保护氨基醇，其中随后可以裂解苄醚以产生BOC保护的氨基醇。因此，各种分子支架具有1,3-关系之间的 o </ i> - 和 n </ i> - 从亚甲醇加入到α，β-不饱和腈中的官能团中可访问官能组。 </ 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-16041/'>《ChemCatChem》</a> <b style="margin: 0 2px;">|</b><span>2018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"> </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/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></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=oxa-Michael addition&option=203" rel="nofollow">oxa-Michael addition;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=amino alcohols&option=203" rel="nofollow">amino alcohols;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=hydrogenation&option=203" rel="nofollow">hydrogenation;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=nitriles&option=203" rel="nofollow">nitriles;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=pincer ligand&option=203" rel="nofollow">pincer ligand;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=ruthenium&option=203" rel="nofollow">ruthenium;</a> </p> <div class="translation"> 机译：Oxa-michael添加;氨基醇;氢化;腈;钳子配体;钌; </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/0704022057070.html">Oxa‐Michael Addition to α,β‐Unsaturated Nitriles: An Expedient Route to γ‐Amino Alcohols and Derivatives</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> </a> <a href="/journal-foreign-16041/" target="_blank" rel="nofollow" class="tuijian_authcolor">ChemCatChem .</a> <span>2018</span><span>,第13期</span> </span> </div> <p class="zwjiyix translation" style="max-width: 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<span> . 2008</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/020314061642.html">含不饱和键环三磷腈衍生物的制备及其对PET阻燃性能的研究</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=潘峰&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 潘峰</a> <span> . 2015</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/06120113770914.html">α,β-不饱和氨基酸衍生物及其DL-硒-甲基硒代氨基酸衍生物、合成方法和应用</a> <b>[P]</b> . <span> 中国专利： CN113773229A </span> <span> . 2021-12-10</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06120615385.html">降低含有氨基腈、二胺、二腈或其混合物的混合物中的不饱和胺含量的方法</a> <b>[P]</b> . <span> 中国专利： CN1656060B </span> <span> . 2010.05.26</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130465383694.html">NEW 3-AMINO-2-HYDROXYBORNANE DERIVATIVE, ASYMMETRIC MICHAEL ADDITION AND PRODUCTION OF OPTICALLY ACTIVE MUSCONE</a> <b>[P]</b> . <span> 外国专利：  JPH03236357A </span> <span> . 1991-10-22</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：新的3-氨基-2-羟基硼烷衍生物，不对称迈克尔加成和光学活性基团的生产 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130489541326.html">Preparation of tertiary alcohols and nitriles by addition of secondary alcohols and nitriles to acetylene</a> <b>[P]</b> . <span> 外国专利：  US3256315A </span> <span> . 1966-06-14</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：通过向乙炔中添加仲醇和腈来制备叔醇和腈 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130459811848.html">3 - amino - 2 - hydroxynorbornan derivatives, asymmetric michael reaction and method for producing the optically active muscon with the michael reaction.</a> <b>[P]</b> . <span> 外国专利：  DE69007756D1 </span> <span> . 1994-05-05</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：3-氨基-2-羟基降冰片烯衍生物，不对称迈克尔反应和利用迈克尔反应生产旋光muscon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('0704022057070','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" 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