Asymmetric Hydrogenation of Polysubstituted Aromatic Ketones Catalyzed by the DIPSkewphos/PICA Derivative–Ruthenium(II) Complexes

Utsumi Noriyuki; Arai Noriyoshi; Kawaguchi Kei; Katayama Takeaki; Yasuda Toshihisa; Murata Kunihiko; Ohkuma Takeshi

摘要

Abstract > The DIPSkewphos/PICA derivative‐Ru(II) complexes catalyzed asymmetric hydrogenation of significantly sterically hindered 2’,3’,4’,5’,6’‐pentamethylacetophenone, which was not reduced with NaBH <sub>4</sub> at 25?°C, with a substrate‐to‐catalyst molar ratio (S/C) of 2000 under 50?atm of H <sub>2</sub> in a base‐containing 2‐propanol to afford the alcohol in 99?% ee quantitatively. A series of polysubstituted aromatic ketones was smoothly reacted with an S/C of 300–10,000 under 10–50?atm of H <sub>2</sub> , yielding the alcoholic products in up to 99?% ee . The catalyst system achieved an industrial‐scale (50?kg) hydrogenation of 2’,6’‐dichloro‐3’‐fluoroacetophenone, affording the alcohol in 96?% isolated yield and in 98?% ee . The obtained alcoholic product is known as a key intermediate for the synthesis of the medicine crizotinib. </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> > Dipskewphos / PICA衍生物-Ru（II）复合物催化的不对称氢化明显的空间阻碍2'，3'，4'，5'，6'-五甲基乙酮酮，其不会用纳米降低 <sub> 4 </ sub> 在25℃，2000℃下的基质到催化剂摩尔比（S / C）为50℃以下 <sub> 2 </ sub> 在含碱的2-丙醇中，在99？％中提供酒精 ee </ i> 数量上。将一系列多助化芳香酮平滑地反应300-10,000以下10-50℃的S / C. <sub> 2 </ sub> ，含酒精产品高达99？％ ee </ i> 。催化剂体系实现了2'，6'-二氯-3'-氟代戊酰胺的工业规模（50μl）氢化，得到了96μl％分离的产率的醇，98？％ ee </ i> 。所得酒精产物称为用于合成药物克里齐替尼的关键中间体。 </ 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18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=Utsumi Noriyuki&option=202" target="_blank" rel="nofollow">Utsumi Noriyuki;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Arai Noriyoshi&option=202" target="_blank" rel="nofollow">Arai Noriyoshi;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Kawaguchi Kei&option=202" target="_blank" rel="nofollow">Kawaguchi Kei;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Katayama Takeaki&option=202" target="_blank" rel="nofollow">Katayama Takeaki;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Yasuda Toshihisa&option=202" target="_blank" rel="nofollow">Yasuda Toshihisa;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Murata Kunihiko&option=202" target="_blank" rel="nofollow">Murata Kunihiko;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Ohkuma Takeshi&option=202" target="_blank" rel="nofollow">Ohkuma Takeshi;</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>Central Research Laboratory Technology and Development DivisionKanto Chemical Co. Inc. SokaSaitama 340-0003 Japan;</p> <p>Division of Applied Chemistry and Frontier Chemistry Center Faculty of EngineeringHokkaido UniversityHokkaido 060-8628 Japan;</p> <p>Division of Applied Chemistry and Frontier Chemistry Center Faculty of EngineeringHokkaido UniversityHokkaido 060-8628 Japan;</p> <p>Central Research Laboratory Technology and Development DivisionKanto Chemical Co. Inc. SokaSaitama 340-0003 Japan;</p> <p>Central Research Laboratory Technology and Development DivisionKanto Chemical Co. Inc. SokaSaitama 340-0003 Japan;</p> <p>Central Research Laboratory Technology and Development DivisionKanto Chemical Co. Inc. SokaSaitama 340-0003 Japan;</p> <p>Division of Applied Chemistry and Frontier Chemistry Center Faculty of EngineeringHokkaido UniversityHokkaido 060-8628 Japan;</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/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=alcohol&option=203" rel="nofollow">alcohol;</a> <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=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=ketone&option=203" rel="nofollow">ketone;</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：酒精;不对称催化;氢化;酮;钌; </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" 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解永树</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=寇福平&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,寇福平</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=林瑞森&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,林瑞森</a> <span> <a href="/journal-cn-15070/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 无机化学学报 </a> </span> <span> . 2000</span><span>,第003期</span> </span> </div> </li> <li> <div> <b>6. </b><a class="enjiyixqcontent" href="/academic-conference-cn_meeting-22303_thesis/02022591606.html">PEG-水介质中水溶性钌膦配合物催化芳香酮的不对称加氢反应</a> <b>[C]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=王金渡&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 王金渡</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=冯建&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,冯建</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=杨朝芬&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,杨朝芬</a> <span> <a href="/conference-cn-22303/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 中国化学会第十届全国络合催化学术讨论会 </a> <span> <span> . 2007</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/020314500404.html">手性化合物修饰的负载型铑、钌催化剂和钌膦配合物催化丙酮酸乙酯与芳香酮的不对称加氢</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=熊伟&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 熊伟</a> <span> . 2005</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/061203500770.html">一种钌(II)配合物、钌(II)配合物-TiO2功能膜及其应用</a> <b>[P]</b> . <span> 中国专利： CN107286198B </span> <span> . 2019.10.11</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06120109789542.html">一种钌(II)配合物、钌(II)配合物‑TiO2功能膜及其应用</a> <b>[P]</b> . <span> 中国专利： CN107286198A </span> <span> . 2017-10-24</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130461191209.html">Asymmetric hydrogenation of aromatic-substituted olefins using cationic ruthenium(III) complexes</a> <b>[P]</b> . <span> 外国专利：  US5177231A </span> <span> . 1993-01-05</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：使用阳离子钌（III）配合物对芳族取代烯烃进行不对称氢化 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130432837012.html">The reaction products of high melting point, exempt from tin, resin aldeu00ecdo carbonyl hydrogenated ketone - resins, hydrogenated ketone resins, as well as aldeu00ecdo carbonyl hydrogenated ketone - based and nu00facle - hydrogenated aromatic ketones and poliisocianatos</a> <b>[P]</b> . <span> 外国专利：  BRPI0513463A </span> <span> . 2008-05-06</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：高熔点，不含锡的反应产物，醛基羰基氢化酮树脂，氢化酮树脂以及醛基羰基氢化酮和芳烃基氢化芳族酮和聚硅氧烷的反应产物 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130423600787.html">Carbonyl the ketone - aldehyde resin which hydrogenates, the carbonyl - which designates ketone resin, and the aromatic ketone which hydrogenate as the foundation and ring the high melting point reaction product null of tin non- containing from of ketone - aldehyde resin and poriisoshianeto which hydrogenate</a> <b>[P]</b> . <span> 外国专利：  JP4909270B2 </span> <span> . 2012-04-04</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：将氢化的酮-醛树脂羰基，羰基的酮羰基和氢化的芳族酮的羰基-醛树脂与氢化的对苯三甲磺酸的高熔点反应产物归零 </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('0704022060099','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" onclick="$('.journalsub-pop-up').hide()"> <p class="pardon">抱歉，该期刊暂不可订阅，敬请期待！</p> <p class="current">目前支持订阅全部北京大学中文核心（2020）期刊目录。</p> <div style="display: flex;margin-top: 69px;justify-content: space-between;"> 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