• 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

通过 N-杂环卡宾催化双酚的不对称去对称化来获得 P-手性膦酸酯。

Access to P-Stereogenic Phosphinates via N-Heterocyclic Carbene-Catalyzed Desymmetrization of Bisphenols.

机构信息

Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University , Singapore 637371, Singapore.

Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University , Huaxi District, Guiyang 550025, China.

出版信息

J Am Chem Soc. 2016 Jun 22;138(24):7524-7. doi: 10.1021/jacs.6b04624. Epub 2016 Jun 10.

DOI:10.1021/jacs.6b04624
PMID:27286229
Abstract

A carbene-catalyzed desymmetrization of prochiral bisphenol compounds bearing remote P-stereogenic centers is disclosed. The catalytic reactions can be performed on gram scales with 1 mol % N-heterocyclic carbene (NHC) catalyst, providing efficient access to enantiomerically enriched P-stereogenic phosphinates. The chiral phosphinates prepared with our method can find widespread applications as asymmetric organic catalysts and ligands.

摘要

本文报道了一种手性卡宾催化的具有远程 P 手性中心的前手性双酚化合物的去对称化反应。催化反应可以在克级规模下,以 1 mol% 的 N-杂环卡宾(NHC)催化剂进行,为对映体富集的 P 手性膦酸酯提供了有效的合成途径。本方法制备的手性膦酸酯可广泛用作不对称有机催化剂和配体。

相似文献

1
Access to P-Stereogenic Phosphinates via N-Heterocyclic Carbene-Catalyzed Desymmetrization of Bisphenols.通过 N-杂环卡宾催化双酚的不对称去对称化来获得 P-手性膦酸酯。
J Am Chem Soc. 2016 Jun 22;138(24):7524-7. doi: 10.1021/jacs.6b04624. Epub 2016 Jun 10.
2
N-Heterocyclic carbene-catalyzed desymmetrization of functionalized 1,4-dienes via Stetter Reaction.通过施陶丁格反应实现N-杂环卡宾催化的官能化1,4-二烯的去对称化反应。
Chem Commun (Camb). 2016 May 11;52(38):6459-62. doi: 10.1039/c6cc01011c. Epub 2016 Apr 21.
3
Enantioselective and Regioselective Hydroetherification of Alkynes by Gold-Catalyzed Desymmetrization of Prochiral Phenols with P-Stereogenic Centers.手性金催化前手性酚的不对称去对称化实现炔烃的对映选择性和区域选择性氢醚化反应。
Org Lett. 2018 Nov 16;20(22):7039-7043. doi: 10.1021/acs.orglett.8b02982. Epub 2018 Oct 29.
4
Chiral N-Heterocyclic-Carbene-Catalyzed Cascade Asymmetric Desymmetrization of Cyclopentenediones with Enals: Access to Optically Active 1,3-Indandione Derivatives.手性 N-杂环卡宾催化环戊二酮与烯醛的串联不对称去对称化反应:合成光学活性 1,3-茚二酮衍生物
Org Lett. 2019 Nov 1;21(21):8582-8586. doi: 10.1021/acs.orglett.9b03178. Epub 2019 Oct 16.
5
Ionic Hydrogen Bond-Assisted Catalytic Construction of Nitrogen Stereogenic Center via Formal Desymmetrization of Remote Diols.离子氢键辅助催化通过远程二醇的形式去对称化构建氮立体中心。
Angew Chem Int Ed Engl. 2024 Jul 29;63(31):e202404979. doi: 10.1002/anie.202404979. Epub 2024 Jun 25.
6
Desymmetrization of Cyclic 1,3-Diketones under -Heterocyclic Carbene Organocatalysis: Access to Organofluorines with Multiple Stereogenic Centers.- 杂环卡宾有机催化下环状1,3 - 二酮的去对称化反应:构建具有多个手性中心的有机氟化物
Research (Wash D C). 2021 Aug 23;2021:9867915. doi: 10.34133/2021/9867915. eCollection 2021.
7
N-Heterocyclic Carbene-Catalyzed Desymmetrization of Siladials To Access Silicon-Stereogenic Organosilanes.N-杂环卡宾催化硅双醛的去对称化反应以合成含硅手性中心的有机硅烷。
J Org Chem. 2022 Dec 2;87(23):16127-16137. doi: 10.1021/acs.joc.2c02184. Epub 2022 Nov 17.
8
Desymmetrization of Phosphinic Acids via Pd-Catalyzed Asymmetric Allylic Alkylation: Rapid Access to -Chiral Phosphinates.通过钯催化的不对称烯丙基烷基化反应实现膦酸的去对称化:快速获得 -手性膦酸酯。
J Am Chem Soc. 2019 Sep 11;141(36):14098-14103. doi: 10.1021/jacs.9b07340. Epub 2019 Aug 27.
9
Carbene-Catalyzed Desymmetrization and Direct Construction of Arenes with All-Carbon Quaternary Chiral Center.卡宾催化的非对映选择性和直接构建具有全碳季碳手性中心的芳烃。
Angew Chem Int Ed Engl. 2019 Oct 28;58(44):15778-15782. doi: 10.1002/anie.201910183. Epub 2019 Sep 19.
10
Enantioselective Synthesis of Axially Chiral Diaryl Ethers via NHC Catalyzed Desymmetrization and Following Resolution.通过氮杂环卡宾催化的去对称化及后续拆分实现轴手性二芳基醚的对映选择性合成。
Angew Chem Int Ed Engl. 2024 Jan 22;63(4):e202314228. doi: 10.1002/anie.202314228. Epub 2023 Dec 11.

引用本文的文献

1
Asymmetric synthesis of P-stereogenic phosphindane oxides via kinetic resolution and their biological activity.通过动力学拆分对映选择性合成 P-手性膦茚氧化物及其生物活性。
Nat Commun. 2024 Mar 21;15(1):2548. doi: 10.1038/s41467-024-46892-7.
2
Diastereoselective Formal 1,3-Dipolar Cycloaddition of Trifluoroethyl Amine-Derived Ketimines Enables the Desymmetrization of Cyclopentenediones.三氟乙胺衍生的酮亚胺的非对映选择性形式1,3-偶极环加成反应实现了环戊二酮的去对称化。
Molecules. 2023 Jul 13;28(14):5372. doi: 10.3390/molecules28145372.
3
Organocatalytic asymmetric synthesis of P-stereogenic molecules.
P-手性分子的有机催化不对称合成。
Front Chem. 2023 Feb 16;11:1132025. doi: 10.3389/fchem.2023.1132025. eCollection 2023.
4
Access to Enantiomerically Pure P-Stereogenic Primary Aminophosphine Sulfides under Reductive Conditions.在还原条件下获得对映体纯 P-手性伯膦硫醚。
Chemistry. 2022 Dec 27;28(72):e202202608. doi: 10.1002/chem.202202608. Epub 2022 Oct 28.
5
Desymmetrization of N-Cbz glutarimides through N-heterocyclic carbene organocatalysis.通过氮杂环卡宾有机催化实现 N-苄氧羰基戊二酰亚胺的去对称化反应。
Nat Commun. 2022 Jul 13;13(1):4042. doi: 10.1038/s41467-022-31760-z.
6
Synthesis of -Heteroarenemethyl Esters via C-C Bond Cleavage of Acyl Cyanides Under Transition Metal-Free Conditions.在无过渡金属条件下通过酰基氰的C-C键裂解合成α-杂芳烃甲酯
Front Chem. 2022 Jan 27;9:822625. doi: 10.3389/fchem.2021.822625. eCollection 2021.
7
A chiroptical approach for the absolute stereochemical determination of -stereogenic centers.一种用于绝对立体化学测定 - 立体中心的旋光方法。
Chem Sci. 2020 Dec 7;12(5):1750-1755. doi: 10.1039/d0sc02940h.
8
Access to -stereogenic compounds desymmetrizing enantioselective bromination.获取用于对映选择性溴化去对称化的手性化合物。
Chem Sci. 2021 Feb 12;12(12):4582-4587. doi: 10.1039/d0sc07008d.
9
Access to -chiral - and -phosphine oxides enabled by Le-Phos-catalyzed asymmetric kinetic resolution.通过勒-磷催化的不对称动力学拆分实现对手性膦氧化物的获取。
Chem Sci. 2020 Sep 2;11(36):9983-9988. doi: 10.1039/d0sc04041j.
10
Enantioselective synthesis of -chiral tertiary phosphine oxides with an ethynyl group Cu(i)-catalyzed azide-alkyne cycloaddition.含乙炔基的手性叔膦氧化物的对映选择性合成:铜(I)催化的叠氮化物-炔烃环加成反应
Chem Sci. 2019 Nov 6;11(1):97-106. doi: 10.1039/c9sc04938j. eCollection 2020 Jan 7.