Rapid Synthesis of Chiral 1,2‐Bisphosphine Derivatives through Copper(I)‐Catalyzed Asymmetric Conjugate Hydrophosphination

Yue Wen‐Jun; Xiao Jun‐Zhao; Zhang Shuai; Yin Liang

摘要

Abstract > 1,2‐Bisphosphines have been identified as one class of important and powerful chiral ligands in asymmetric catalysis with transition metals. Herein, a copper(I)‐catalyzed asymmetric hydrophosphination of α,β‐unsaturated phosphine sulfides was developed with the assistance of “soft–soft” interaction between copper(I)‐catalyst and the phosphine sulfide moiety, which afforded 1,2‐bisphosphine derivatives with diversified electronic nature and steric hindrance in high to excellent yields with high to excellent enantioselectivity. Moreover, the challenging catalytic asymmetric hydrophosphination/protonation reaction was achieved with excellent enantioselectivity. Strikingly, the dynamic kinetic resolution of racemic diarylphosphines was also successfully carried out with high to excellent diastereo‐ and enantioselectivities. Interestingly, the nucleophilic copper(I)‐diphenylphosphide species was characterized by 31 P?NMR spectrum and mass spectrum. At last, three products were transformed to chiral 1,2‐bisphosphines, which were employed as ligands in Rh‐catalyzed asymmetric hydrogenation of α‐amino‐α,β‐unsaturated ester. The α‐amino acid derivative was produced in high enantioselectivity, which demonstrated the utility of the present methodology. </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> > 1,2-二膦已被鉴定为具有过渡金属的不对称催化的一类重要和强大的手性配体。在此，在铜（I）之间的“软软”相互作用 - 催化剂和膦硫化物部分之间的辅助和磷酸硫部分的辅助α，β-不饱和膦硫化物的铜（I）的催化不对称磷化膦酰胺。二膦衍生物具有多样化的电子性质和空间障碍，高于优异的产量，高于优异的对映选择性。此外，通过优异的对映选择性实现了挑战性催化不对称疏水膦膦/质子化反应。引人注目的是，外消旋二芳基膦的动态动力学分辨率也成功地进行了高度至优异的非对映的和对映选择性。有趣的是，亲核铜（I） - 二苯基微晶物质的特征在于 31 </ sup> p？NMR光谱和质谱。最后，将三种产物转化为手性1,2-双膦，其用作Rh催化的α-氨基-α，β-不饱和酯的RH催化的不对称氢化的配体。 α-氨基酸衍生物在高对映射性中产生，这证明了本方法的效用。 </ 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-19011/'>《Angewandte Chemie》</a> <b style="margin: 0 2px;">|</b><span>2020年第18期</span><b style="margin: 0 2px;">|</b><span>共6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=Yue Wen‐Jun&option=202" target="_blank" rel="nofollow">Yue Wen‐Jun;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Xiao Jun‐Zhao&option=202" target="_blank" rel="nofollow">Xiao Jun‐Zhao;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Zhang Shuai&option=202" target="_blank" rel="nofollow">Zhang Shuai;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Yin Liang&option=202" target="_blank" rel="nofollow">Yin Liang;</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>CAS Key Laboratory of Synthetic Chemistry of Natural SubstancesChinese Academy of Sciences345 Lingling Road Shanghai 200032 China;</p> <p>CAS Key Laboratory of Synthetic Chemistry of Natural SubstancesChinese Academy of Sciences345 Lingling Road Shanghai 200032 China;</p> <p>CAS Key Laboratory of Synthetic Chemistry of Natural SubstancesChinese Academy of Sciences345 Lingling Road Shanghai 200032 China;</p> <p>CAS Key Laboratory of Synthetic Chemistry of Natural SubstancesChinese Academy of Sciences345 Lingling Road Shanghai 200032 China;</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/1188.html" title="应用化学">应用化学;</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=1&option=203" rel="nofollow">1;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=2-bisphosphine&option=203" rel="nofollow">2-bisphosphine;</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=chiral ligand&option=203" rel="nofollow">chiral ligand;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=copper catalyst&option=203" rel="nofollow">copper catalyst;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=hydrophosphination&option=203" rel="nofollow">hydrophosphination;</a> </p> <div class="translation"> 机译：1;2-双膦;不对称催化;手性配体;铜催化剂;磷化膦; </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/0704028161311.html">Rapid Synthesis of Chiral 1,2‐Bisphosphine Derivatives through Copper(I)‐Catalyzed Asymmetric Conjugate Hydrophosphination</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Yue Wen‐Jun&option=202" target="_blank" rel="nofollow" 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Buchwald </a> <span>2004</span> </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：不对称催化特征第二部分：铜催化不对称共轭还原反应作为新型β-氮杂杂环酸衍生物的途径</span> </p> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/open-access_resources_thesis/01000132163982.html">Synthesis of chiral anti-1,2-diamine derivatives through copper(I)-catalyzed asymmetric α-addition of ketimines to aldimines</a> <b>[O] </b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Xu-Cheng Gan&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Xu-Cheng Gan,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Cheng-Yuan Zhang&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Cheng-Yuan Zhang,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Feng Zhong&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Feng Zhong,</a> <span>2020</span> </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：通过铜（I）对手性抗1,2-二胺衍生物的合成 - 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Li Chun</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=李春&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,李春</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Li Weixun&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,Li Weixun</a> <span> <a href="/conference-cn-6670/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 第十七届全国金属有机化学学术讨论会 </a> <span> <span> . 2012</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/020315038680.html">手性二胺修饰的镍膦配合物和负载型铱催化剂催化苯乙酮及其衍生物不对称加氢反应的研究</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=杨朝芬&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 杨朝芬</a> <span> . 2006</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/06120113700594.html">一种钯/手性配体催化的同时合成膦手性中心二级/三级膦氧化合物的方法</a> <b>[P]</b> . <span> 中国专利： CN113861238A </span> <span> . 2021-12-31</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06120104419688.html">由含环状手性膦配位体的过渡金属配合物催化的不对称合成</a> <b>[P]</b> . <span> 中国专利： CN1225095A </span> <span> . 1999-08-04</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130469877674.html">NOVEL CHIRAL COPPER COMPLEX AND ASYMMETRIC SYNTHESIS OF CYCLOPROPANECARBOXYLATE DERIVATIVES USING SAID COMPLEX AS CATALYST</a> <b>[P]</b> . <span> 外国专利：  DE3461374D1 </span> <span> . 1987-01-08</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：所说的配合物作为催化剂的新型手性铜配合物和不对称合成环丙烷甲酸酯的衍生物 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130471043483.html">ASYMMETRIC SYNTHESIS OF CYCLOPROPANECARBOXYLATE DERIVATIVES USING CHIRAL COPPER COMPLEX AS CATALYST</a> <b>[P]</b> . <span> 外国专利：  US4603218A </span> <span> . 1986-07-29</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：手性铜配合物催化不对称合成环丙烷羧酸酯 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130470084045.html">Novel chiral copper complex and asymmetric synthesis of cyclopropanecarboxylate derivatives using said complex as catalyst</a> <b>[P]</b> . <span> 外国专利：  EP0128012B1 </span> <span> . 1986-11-20</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：新型手性铜配合物和使用该配合物作为催化剂的不对称合成环丙烷羧酸酯衍生物 </span> </p> </li> </ul> </div> </div> </div> <div class="theme cardcommon" style="overflow: auto;display:none"> <h3 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