• 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

2,2'-二取代氟化联萘衍生物的合成方法及其作为手性单磷酸催化剂设计中手性源的应用

Synthetic Method for 2,2'-Disubstituted Fluorinated Binaphthyl Derivatives and Application as Chiral Source in Design of Chiral Mono-Phosphoric Acid Catalyst.

作者信息

Momiyama Norie, Okamoto Hiroshi, Shimizu Masahiro, Terada Masahiro

机构信息

Department of Life and Coordination-Complex Molecular Science, Institute for Molecular Science Graduate School of Physical Sciences, Graduate University for Advanced Studies (SOKENDAI), Okazaki Aichi, Japan.

Department of Chemistry, Graduate School of Science, Tohoku University, Sendai, Miyagi, Japan.

出版信息

Chirality. 2015 Aug;27(8):464-75. doi: 10.1002/chir.22429. Epub 2015 Feb 9.

DOI:10.1002/chir.22429
PMID:25665035
Abstract

A practical synthetic method for 2,2'-disubstituted fluorinated binaphthyl derivatives was achieved using magnesium bis(2,2,6,6-tetramethylpiperamide) [Mg(TMP)(2)], prepared from LiTMP (2 equiv) and MgBr(2) (1 equiv), which allows for access to a variety of fluorinated binaphthyl compounds. The utility of the fluorinated binaphthyl backbone was evaluated in F10 BINOL derived chiral mono-phosphoric acid (R)- as the chiral Brønsted acid catalyst. The catalyst (R)- performs exceptionally well in the catalytic enantioselective imino-ene reaction, demonstrating the potential of a fluorinated binaphthyl framework.

摘要

使用由双(2,2,6,6 - 四甲基哌啶酰胺)锂(LiTMP,2当量)和溴化镁(MgBr₂,1当量)制备的双(2,2,6,6 - 四甲基哌啶酰胺)镁[Mg(TMP)₂],实现了一种实用的合成2,2'-二取代氟化联萘衍生物的方法,该方法可用于制备多种氟化联萘化合物。在F10 BINOL衍生的手性单磷酸(R) - 作为手性布朗斯特酸催化剂中评估了氟化联萘骨架的效用。催化剂(R) - 在催化对映选择性亚氨基 - 烯反应中表现出色,证明了氟化联萘骨架的潜力。

相似文献

1
Synthetic Method for 2,2'-Disubstituted Fluorinated Binaphthyl Derivatives and Application as Chiral Source in Design of Chiral Mono-Phosphoric Acid Catalyst.2,2'-二取代氟化联萘衍生物的合成方法及其作为手性单磷酸催化剂设计中手性源的应用
Chirality. 2015 Aug;27(8):464-75. doi: 10.1002/chir.22429. Epub 2015 Feb 9.
2
Design of chiral bis-phosphoric acid catalyst derived from (R)-3,3'-di(2-hydroxy-3-arylphenyl)binaphthol: catalytic enantioselective Diels-Alder reaction of α,β-unsaturated aldehydes with amidodienes.(R)-3,3'-二(2-羟基-3-芳基)联萘酚衍生的手性双膦酸催化剂的设计:α,β-不饱和醛与酰胺二烯的催化对映选择性 Diels-Alder 反应。
J Am Chem Soc. 2011 Dec 7;133(48):19294-7. doi: 10.1021/ja2081444. Epub 2011 Nov 11.
3
DFT study of chiral-phosphoric-acid-catalyzed enantioselective Friedel-Crafts reaction of indole with nitroalkene: bifunctionality and substituent effect of phosphoric acid.DFT 研究手性磷酸催化的吲哚与硝基烯烃的不对称 Friedel-Crafts 反应:磷酸的双功能和取代基效应。
Chem Asian J. 2011 Feb 1;6(2):510-6. doi: 10.1002/asia.201000596. Epub 2010 Dec 22.
4
Phase-transfer-catalyzed asymmetric synthesis of axially chiral anilides.相转移催化不对称合成轴手性苯胺。
Chem Asian J. 2013 Dec;8(12):3214-21. doi: 10.1002/asia.201301036. Epub 2013 Sep 20.
5
Pyridinium 1,1'-binaphthyl-2,2'-disulfonates as highly effective chiral Brønsted acid-base combined salt catalysts for enantioselective Mannich-type reaction.吡啶鎓 1,1'-联萘-2,2'-二磺酸盐作为对映选择性曼尼希型反应的高效手性布朗斯特酸碱复合盐催化剂。
J Am Chem Soc. 2008 Dec 17;130(50):16858-60. doi: 10.1021/ja806875c.
6
Design of binaphthyl-modified symmetrical chiral phase-transfer catalysts: substituent effect of 4,4',6,6'-positions of binaphthyl rings in the asymmetric alkylation of a glycine derivative.联萘修饰的对称手性相转移催化剂的设计:联萘环4,4',6,6'-位取代基对甘氨酸衍生物不对称烷基化反应的影响
Chem Asian J. 2007 Oct 1;2(10):1276-81. doi: 10.1002/asia.200700117.
7
Synthesis and catalytic activity of group 5 metal amides with chiral biaryldiamine-based ligands.手性联苯二胺基配体的第 5 族金属酰胺的合成及催化活性。
Dalton Trans. 2011 Feb 21;40(7):1547-66. doi: 10.1039/c0dt01229g. Epub 2011 Jan 10.
8
FBINOL-derived chiral phosphoric acid-catalyzed enantioselective carbonyl-ene reaction: theoretical elucidation of stereochemical outcomes.源自FBINOL的手性磷酸催化的对映选择性羰基-烯反应:立体化学结果的理论阐释
Chem Sci. 2018 Nov 19;10(5):1426-1433. doi: 10.1039/c8sc03587c. eCollection 2019 Feb 7.
9
Chiral metallocycles: rational synthesis and novel applications.手性金属环:合理合成与新颖应用。
Acc Chem Res. 2008 Apr;41(4):521-37. doi: 10.1021/ar700216n. Epub 2008 Feb 14.
10
The Brønsted acid catalyzed, enantioselective vinylogous Mannich reaction.布朗斯特酸催化的对映选择性乙烯基曼尼希反应。
Chemistry. 2010 Mar 1;16(9):2806-18. doi: 10.1002/chem.200902537.

引用本文的文献

1
Determination of the pK Value of a Brønsted Acid by F NMR Spectroscopy.通过氟核磁共振光谱法测定布朗斯特酸的pK值
Magn Reson Chem. 2025 Jan;63(1):17-23. doi: 10.1002/mrc.5485. Epub 2024 Oct 16.
2
FBINOL-derived chiral phosphoric acid-catalyzed enantioselective carbonyl-ene reaction: theoretical elucidation of stereochemical outcomes.源自FBINOL的手性磷酸催化的对映选择性羰基-烯反应:立体化学结果的理论阐释
Chem Sci. 2018 Nov 19;10(5):1426-1433. doi: 10.1039/c8sc03587c. eCollection 2019 Feb 7.