• 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

相转移条件下邻二醇的烷基化动力学拆分:手性硼酸铵催化

Alkylative kinetic resolution of vicinal diols under phase-transfer conditions: a chiral ammonium borinate catalysis.

作者信息

Pawliczek Martin, Hashimoto Takuya, Maruoka Keiji

机构信息

Department of Chemistry , Graduate School of Science , Kyoto University , Sakyo , Kyoto , 606-8502 , Japan . Email:

出版信息

Chem Sci. 2017 Dec 12;9(5):1231-1235. doi: 10.1039/c7sc04854h. eCollection 2018 Feb 7.

DOI:10.1039/c7sc04854h
PMID:29675168
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5885781/
Abstract

Herein, we report the first alkylative kinetic resolution of vicinal alcohols realized by cooperative use of a chiral quaternary ammonium salt and an achiral borinic acid. In addition, a catalytic regioselective alkylation of a secondary alcohol in the presence of an unprotected primary one is presented, emphasizing the unique selectivity and potential of this ammonium borinate catalysis.

摘要

在此,我们报道了首例通过手性季铵盐与非手性硼酸协同作用实现的邻二醇的烷基化动力学拆分。此外,还展示了在未保护的伯醇存在下仲醇的催化区域选择性烷基化反应,强调了这种硼酸铵催化的独特选择性和潜力。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4030/5885781/ff901d7f271a/c7sc04854h-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4030/5885781/feea63a22b56/c7sc04854h-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4030/5885781/693087420f2a/c7sc04854h-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4030/5885781/3aa74c6de93f/c7sc04854h-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4030/5885781/ff901d7f271a/c7sc04854h-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4030/5885781/feea63a22b56/c7sc04854h-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4030/5885781/693087420f2a/c7sc04854h-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4030/5885781/3aa74c6de93f/c7sc04854h-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4030/5885781/ff901d7f271a/c7sc04854h-s2.jpg

相似文献

1
Alkylative kinetic resolution of vicinal diols under phase-transfer conditions: a chiral ammonium borinate catalysis.相转移条件下邻二醇的烷基化动力学拆分:手性硼酸铵催化
Chem Sci. 2017 Dec 12;9(5):1231-1235. doi: 10.1039/c7sc04854h. eCollection 2018 Feb 7.
2
Highly enantioselective phase-transfer-catalyzed alkylation of protected alpha-amino acid amides toward practical asymmetric synthesis of vicinal diamines, alpha-amino ketones, and alpha-amino alcohols.用于邻二胺、α-氨基酮和α-氨基醇的实用不对称合成的受保护α-氨基酸酰胺的高对映选择性相转移催化烷基化反应。
J Am Chem Soc. 2005 Apr 13;127(14):5073-83. doi: 10.1021/ja0459328.
3
Synthesis of a -Symmetric Chiral Borinic Acid and Its Application in Catalytic Desymmetrization of 2,2-Disubstituted-1,3-Propanediols.α-对称手性硼酸的合成及其在2,2-二取代-1,3-丙二醇催化去对称化反应中的应用。
J Am Chem Soc. 2023 Apr 10. doi: 10.1021/jacs.3c02331.
4
Regioselective, borinic acid-catalyzed monoacylation, sulfonylation and alkylation of diols and carbohydrates: expansion of substrate scope and mechanistic studies.区域选择性硼酸催化的二醇和碳水化合物的单酰化、磺酰化和烷基化反应:底物范围的扩展和机理研究。
J Am Chem Soc. 2012 May 16;134(19):8260-7. doi: 10.1021/ja302549c. Epub 2012 Apr 25.
5
A trifunctional catalyst for one-pot synthesis of chiral diols via Heck coupling-N-oxidation-asymmetric dihydroxylation: application for the synthesis of diltiazem and taxol side chain.一种用于通过Heck偶联-N-氧化-不对称二羟基化一锅法合成手性二醇的三功能催化剂:在合成地尔硫卓和紫杉醇侧链中的应用。
J Org Chem. 2003 Mar 7;68(5):1736-46. doi: 10.1021/jo026687i.
6
Construction of a chiral quaternary carbon center by catalytic asymmetric alkylation of 2-arylcyclohexanones under phase-transfer conditions.手性季碳中心的构建通过相转移条件下 2-芳基环己酮的催化不对称烷基化反应。
J Am Chem Soc. 2013 May 15;135(19):7134-7. doi: 10.1021/ja403340r. Epub 2013 May 2.
7
Chemoselective Pd-catalyzed oxidation of polyols: synthetic scope and mechanistic studies.钯催化多元醇的选择性氧化:合成范围和机理研究。
J Am Chem Soc. 2013 May 22;135(20):7593-602. doi: 10.1021/ja4008694. Epub 2013 May 9.
8
Catalytic Diastereo- and Enantioconvergent Synthesis of Vicinal Diamines from Diols through Borrowing Hydrogen.通过借氢实现二醇构建手性邻二胺的催化非对映和对映选择性合成。
Angew Chem Int Ed Engl. 2021 Aug 16;60(34):18599-18604. doi: 10.1002/anie.202101517. Epub 2021 Jul 16.
9
The versatile roles of ammonium salt catalysts in enantioselective reduction and alkylation of α,β-unsaturated aldehydes: iminium catalysis, enamine catalysis and acid catalysis.铵盐催化剂在α,β-不饱和醛的对映选择性还原和烷基化反应中的多功能作用:亚胺催化、烯胺催化和酸催化。
Chem Commun (Camb). 2011 May 7;47(17):5007-9. doi: 10.1039/c1cc10124b. Epub 2011 Mar 22.
10
Cooperative Asymmetric Cation-Binding Catalysis.协同不对称阳离子键催化作用。
Acc Chem Res. 2021 Dec 7;54(23):4319-4333. doi: 10.1021/acs.accounts.1c00400. Epub 2021 Nov 16.

引用本文的文献

1
Asymmetric phase-transfer catalysis.不对称相转移催化
Nat Rev Chem. 2024 Nov;8(11):851-869. doi: 10.1038/s41570-024-00642-x. Epub 2024 Oct 9.
2
Chemical approaches to the sulfation of small molecules: current progress and future directions.小分子硫酸化的化学方法:当前进展与未来方向
Essays Biochem. 2024 Dec 4;68(4):449-466. doi: 10.1042/EBC20240001.
3
Kinetic resolution of racemic tertiary allylic alcohols through S2' reaction using a chiral bisphosphoric acid/silver(i) salt co-catalyst system.使用手性双磷酸/银(I)盐共催化剂体系通过S2'反应对外消旋叔烯丙醇进行动力学拆分。

本文引用的文献

1
Catalytic enantioselective synthesis of atropisomeric biaryls by a cation-directed O-alkylation.手性芳基轴手性双芳基的阳离子导向 O-烷基化催化不对称合成
Nat Chem. 2017 Jun;9(6):558-562. doi: 10.1038/nchem.2710. Epub 2017 Jan 23.
2
Enantioselective Propargylation of Polyols and Desymmetrization of meso 1,2-Diols by Copper/Borinic Acid Dual Catalysis.铜/硼酸双催化对多元醇的对映选择性丙炔化和内消旋 1,2-二醇的去对称化。
Angew Chem Int Ed Engl. 2017 Jun 12;56(25):7213-7217. doi: 10.1002/anie.201703029. Epub 2017 May 19.
3
Borinic acid-catalyzed stereo- and site-selective synthesis of β-glycosylceramides.
Chem Sci. 2022 Jul 20;13(33):9607-9613. doi: 10.1039/d2sc03052g. eCollection 2022 Aug 24.
4
Enantioselective Kinetic Resolution/Desymmetrization of -Quinols: A Case Study in Boronic-Acid-Directed Phosphoric Acid Catalysis.α-喹诺醇的对映选择性动力学拆分/去对称化:硼酸导向磷酸催化的案例研究
Adv Synth Catal. 2020 Jan 23;362(2):295-301. doi: 10.1002/adsc.201900816. Epub 2019 Sep 6.
硼酸催化的β-糖基神经酰胺的立体和位点选择性合成。
Chem Commun (Camb). 2017 May 30;53(44):5978-5980. doi: 10.1039/c7cc01673e.
4
Phase-transfer catalyzed asymmetric synthesis of α,β-unsaturated γ,γ-disubstituted γ-lactams.相转移催化的α,β-不饱和γ,γ-二取代γ-内酰胺的不对称合成
Chem Commun (Camb). 2017 Apr 27;53(35):4779-4782. doi: 10.1039/c7cc01058c.
5
Catalytic Site-Selective Acylation of Carbohydrates Directed by Cation-n Interaction.阳离子-π 相互作用导向的碳水化合物催化位点选择性酰化反应。
J Am Chem Soc. 2017 Mar 29;139(12):4346-4349. doi: 10.1021/jacs.7b01412. Epub 2017 Mar 17.
6
Regiodivergent Catalysis: A Powerful Tool for Selective Catalysis.区域发散催化:选择性催化的有力工具。
Chemistry. 2017 Jan 1;23(1):19-32. doi: 10.1002/chem.201603993. Epub 2016 Nov 4.
7
ortho-C-H Arylation of Benzoic Acids with Aryl Bromides and Chlorides Catalyzed by Ruthenium.钌催化的苯甲酸与芳基溴化物和氯化物的邻位 C-H 芳基化反应。
Angew Chem Int Ed Engl. 2016 Nov 14;55(47):14752-14755. doi: 10.1002/anie.201607270. Epub 2016 Oct 21.
8
Borinic Acid Catalyzed Stereo- and Regioselective Couplings of Glycosyl Methanesulfonates.硼酸催化的糖基甲磺酸酯的立体和区域选择性偶联反应。
J Am Chem Soc. 2016 Aug 31;138(34):11058-66. doi: 10.1021/jacs.6b06943. Epub 2016 Aug 17.
9
Organocatalytic enantioselective desymmetrisation.有机催化的对映选择性去对称化。
Chem Soc Rev. 2016 Oct 21;45(20):5474-5540. doi: 10.1039/c5cs00015g. Epub 2016 Jun 27.
10
Enantioselective acyl transfer catalysis by a combination of common catalytic motifs and electrostatic interactions.通过常见催化基序与静电相互作用相结合实现对映选择性酰基转移催化。
Nat Commun. 2016 Apr 15;7:11297. doi: 10.1038/ncomms11297.