• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利：CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法，用中文像聊天一样搜索，搜遍4000万医学文献。AI智能推荐，让科研检索更轻松。

立即免费搜索

文件翻译

保留排版，准确专业，支持PDF/Word/PPT等文件格式，支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述，25分钟生成高质量综述，智能提取关键信息，辅助科研写作。

立即免费体验

使用手性 '-二氧化物/金属配合物的非对映发散性不对称迈克尔烷基化反应。

Diastereodivergent asymmetric Michael-alkylation reactions using chiral ,'-dioxide/metal complexes.

作者信息

Kuang Yulong, Shen Bin, Dai Li, Yao Qian, Liu Xiaohua, Lin Lili, Feng Xiaoming

机构信息

Key Laboratory of Green Chemistry & Technology , Ministry of Education , College of Chemistry , Sichuan University , Chengdu 610064 , China . Email:

Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) , P. R. China.

出版信息

Chem Sci. 2017 Nov 8;9(3):688-692. doi: 10.1039/c7sc02757e. eCollection 2018 Jan 21.

DOI:10.1039/c7sc02757e
PMID:29629137
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5869575/
Abstract

A diastereodivergent asymmetric Michael-alkylation reaction between 3-chloro-oxindoles and β,γ-unsaturated-α-ketoesters has been achieved using /Sc(OTf) and /Mg(OTf) metal complexes as catalysts. Both -(1,2,3) and -(1,2,3) chiral spiro cyclopropane oxindoles were constructed in good yields, diastereoselectivities and ee values. The diastereodivergent control may originate from different alkylation pathways after the Michael addition, with either intramolecular trapping of the aza--xylylene intermediate or direct S2 substitution.

摘要

使用/Sc(OTf)和/Mg(OTf)金属配合物作为催化剂，实现了3-氯氧化吲哚与β,γ-不饱和-α-酮酯之间的非对映发散性不对称迈克尔烷基化反应。-(1,2,3)和-(1,2,3)手性螺环丙烷氧化吲哚均以良好的产率、非对映选择性和对映体过量值构建而成。非对映发散性控制可能源于迈克尔加成后不同的烷基化途径，即氮杂-对二甲苯中间体的分子内捕获或直接的S2取代。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5501/5869575/6a8df0eed9ee/c7sc02757e-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5501/5869575/0f7614cccee4/c7sc02757e-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5501/5869575/800a7dc24503/c7sc02757e-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5501/5869575/6a8df0eed9ee/c7sc02757e-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5501/5869575/0f7614cccee4/c7sc02757e-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5501/5869575/800a7dc24503/c7sc02757e-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5501/5869575/6a8df0eed9ee/c7sc02757e-s2.jpg

相似文献

1
Diastereodivergent asymmetric Michael-alkylation reactions using chiral ,'-dioxide/metal complexes.使用手性 '-二氧化物/金属配合物的非对映发散性不对称迈克尔烷基化反应。
Chem Sci. 2017 Nov 8;9(3):688-692. doi: 10.1039/c7sc02757e. eCollection 2018 Jan 21.
2
Asymmetric Cycloaddition and Cyclization Reactions Catalyzed by Chiral N,N'-Dioxide-Metal Complexes.手性 N,N'-二氧代合金属配合物催化的不对称环加成和环化反应。
Acc Chem Res. 2017 Oct 17;50(10):2621-2631. doi: 10.1021/acs.accounts.7b00377. Epub 2017 Oct 2.
3
Construction of Spirocyclopropane-Linked Heterocycles Containing Both Pyrazolones and Oxindoles through Michael/Alkylation Cascade Reactions.通过迈克尔/烷基化串联反应构建含吡唑啉酮和氧化吲哚的螺环丙烷连接杂环化合物。
J Org Chem. 2015 Nov 20;80(22):11369-77. doi: 10.1021/acs.joc.5b01940. Epub 2015 Nov 2.
4
Chiral N,N'-dioxides: new ligands and organocatalysts for catalytic asymmetric reactions.手性 N,N'-二氧代化合物：用于催化不对称反应的新型配体和有机催化剂。
Acc Chem Res. 2011 Aug 16;44(8):574-87. doi: 10.1021/ar200015s. Epub 2011 Jun 24.
5
Diastereodivergent Catalytic Asymmetric Michael Addition of 2-Oxindoles to α,β-Unsaturated Ketones by Chiral Diamine Catalysts.手性二胺催化剂催化2-氧化吲哚对α,β-不饱和酮的非对映发散性催化不对称迈克尔加成反应
Org Lett. 2015 Jun 5;17(11):2732-5. doi: 10.1021/acs.orglett.5b01149. Epub 2015 May 14.
6
Chiral N,N'-Dioxide/Lanthanide(III) Complex Catalyzed Asymmetric Bisvinylogous Mukaiyama Aldol Reactions.手性 N,N'-二氧/镧系元素（III）配合物催化不对称双烯醇式 Mukaiyama 缩合反应。
Org Lett. 2017 Jan 20;19(2):332-335. doi: 10.1021/acs.orglett.6b03470. Epub 2017 Jan 9.
7
Asymmetric synthesis of 3-spirocyclopropyl-2-oxindoles via intramolecular trapping of chiral aza-ortho-xylylene.通过手性氮杂邻二甲苯的分子内捕获实现 3-螺环丙基-2-氧吲哚的不对称合成。
Chem Commun (Camb). 2013 Oct 14;49(80):9224-6. doi: 10.1039/c3cc45369c. Epub 2013 Aug 30.
8
(S,S)-(+)-pseudoephedrine as chiral auxiliary in asymmetric aza-Michael reactions. Unexpected selectivity change when manipulating the structure of the auxiliary.（S，S）-（+）-伪麻黄碱作为不对称氮杂迈克尔反应中的手性助剂。在对手性助剂结构进行操作时意外的选择性变化。
J Org Chem. 2005 Oct 28;70(22):8790-800. doi: 10.1021/jo051207j.
9
Diastereodivergent Synthesis of α-Chiral Tertiary Azides through Catalytic Asymmetric Michael Addition.通过催化不对称迈克尔加成实现α-手性叔叠氮化物的非对映发散合成
Org Lett. 2020 Nov 6;22(21):8578-8583. doi: 10.1021/acs.orglett.0c03178. Epub 2020 Oct 20.
10
An organocatalytic domino Michael-alkylation reaction: highly enantioselective construction of spiro-cyclopentanoneoxindoles and tetronic acid scaffolds.一种有机催化多米诺迈克尔-烷基化反应：螺环戊酮吲哚酮和特窗酸支架的高对映选择性构建
Chem Commun (Camb). 2014 Dec 4;50(93):14601-4. doi: 10.1039/c4cc05207b.

引用本文的文献

1
Bimetallic Ru/Ru-Catalyzed Asymmetric One-Pot Sequential Hydrogenations for the Stereodivergent Synthesis of Chiral Lactones.双金属钌/钌催化的不对称一锅法连续氢化反应用于手性内酯的立体发散合成。
Adv Sci (Weinh). 2024 Jun;11(23):e2400621. doi: 10.1002/advs.202400621. Epub 2024 Mar 21.
2
Further developments of -unsaturated -ketoesters as versatile synthons in asymmetric catalysis.α,β-不饱和α-酮酯作为不对称催化中通用合成子的进一步发展
iScience. 2022 Feb 11;25(3):103913. doi: 10.1016/j.isci.2022.103913. eCollection 2022 Mar 18.

本文引用的文献

1
Asymmetric Cycloaddition and Cyclization Reactions Catalyzed by Chiral N,N'-Dioxide-Metal Complexes.手性 N,N'-二氧代合金属配合物催化的不对称环加成和环化反应。
Acc Chem Res. 2017 Oct 17;50(10):2621-2631. doi: 10.1021/acs.accounts.7b00377. Epub 2017 Oct 2.
2
Nickel-Catalyzed Conjugate Addition of Silyl Ketene Imines to In Situ Generated Indol-2-ones: Highly Enantioselective Construction of Vicinal All-Carbon Quaternary Stereocenters.镍催化硅基烯酮亚胺与原位生成的吲哚-2-酮的共轭加成：高对映选择性构建偕碳季碳立体中心。
Angew Chem Int Ed Engl. 2017 Oct 9;56(42):13107-13111. doi: 10.1002/anie.201705943. Epub 2017 Sep 8.
3
Nickel(ii)-catalyzed enantioselective cyclopropanation of 3-alkenyl-oxindoles with phenyliodonium ylide free carbene.
镍（II）催化3-烯基氧化吲哚与苯碘叶立德游离卡宾的对映选择性环丙烷化反应。
Chem Sci. 2016 Apr 21;7(4):2717-2721. doi: 10.1039/c5sc03658e. Epub 2016 Jan 4.
4
Switchable divergent asymmetric synthesis via organocatalysis.通过有机催化实现可切换发散不对称合成。
Chem Soc Rev. 2017 Mar 21;46(6):1675-1692. doi: 10.1039/c6cs00247a.
5
Chiral Rhodium(III) Complex-Catalyzed Cascade Michael-Alkylation Reactions: Enantioselective Synthesis of Cyclopropanes.手性铑(III)配合物催化的级联 Michael-烷基化反应：环丙烷的对映选择性合成。
J Org Chem. 2017 Jan 6;82(1):796-803. doi: 10.1021/acs.joc.6b02583. Epub 2016 Dec 27.
6
Catalytic Strategies for Diastereodivergent Synthesis.非对映选择性合成的催化策略
Chemistry. 2017 May 11;23(27):6464-6482. doi: 10.1002/chem.201604617. Epub 2017 Jan 31.
7
Chiral N,N'-Dioxide-Organocatalyzed Regio-, Diastereo- and Enantioselective Michael Addition-Alkylation Reaction.手性N,N'-二氧化物-有机催化的区域、非对映和对映选择性迈克尔加成-烷基化反应
Chemistry. 2016 Oct 24;22(44):15650-15653. doi: 10.1002/chem.201603629. Epub 2016 Sep 30.
8
Diastereodivergent Construction of Bicyclic γ-Lactones via Enantioselective Ketone Hydroacylation.通过对映选择性酮氢酰化反应构建双环γ-内酯的非对映选择性构建。
J Am Chem Soc. 2016 Sep 21;138(37):12013-6. doi: 10.1021/jacs.6b06227. Epub 2016 Sep 1.
9
Construction of Spirocyclopropane-Linked Heterocycles Containing Both Pyrazolones and Oxindoles through Michael/Alkylation Cascade Reactions.通过迈克尔/烷基化串联反应构建含吡唑啉酮和氧化吲哚的螺环丙烷连接杂环化合物。
J Org Chem. 2015 Nov 20;80(22):11369-77. doi: 10.1021/acs.joc.5b01940. Epub 2015 Nov 2.
10
The discovery of Polo-like kinase 4 inhibitors: identification of (1R,2S).2-(3-((E).4-(((cis).2,6-dimethylmorpholino)methyl)styryl). 1H.indazol-6-yl)-5'-methoxyspiro[cyclopropane-1,3'-indolin]-2'-one (CFI-400945) as a potent, orally active antitumor agent.Polo-like 激酶 4 抑制剂的发现：（1R,2S）-2-[3-((E)-4-(((顺式)-2,6-二甲基吗啉基)甲基)亚乙烯基)-1H-吲唑-6-基]-5'-甲氧基螺[环丙烷-1,3'-吲哚]-2'-酮（CFI-400945）的鉴定，作为一种有效的、口服活性的抗肿瘤剂。
J Med Chem. 2015 Jan 8;58(1):147-69.