• 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

异硫脲与布朗斯特酸协同催化:二氢吡啶酮的对映选择性构建

Isothiourea and Brønsted Acid Cooperative Catalysis: Enantioselective Construction of Dihydropyridinones.

作者信息

Zhang Yu-Chen, Geng Rui-Long, Song Jin, Gong Liu-Zhu

机构信息

Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei 230026, China.

出版信息

Org Lett. 2020 Mar 20;22(6):2261-2265. doi: 10.1021/acs.orglett.0c00461. Epub 2020 Mar 2.

DOI:10.1021/acs.orglett.0c00461
PMID:32119556
Abstract

Asymmetric annulation of bench-stable α,β-unsaturated aryl esters with enamines was realized via cooperative catalysis of chiral isothiourea and Brønsted acid. This reaction proceeds via a chiral α,β-unsaturated acyl ammonium intermediate and offers a rapid access to functionalized 3,4-dihydropyridin-2-ones in high yields and excellent enantioselectivities.

摘要

通过手性异硫脲和布朗斯特酸的协同催化,实现了稳定的α,β-不饱和芳基酯与烯胺的不对称环化反应。该反应通过手性α,β-不饱和酰基铵中间体进行,能够快速高效地获得官能化的3,4-二氢吡啶-2-酮,产率高且对映选择性优异。

相似文献

1
Isothiourea and Brønsted Acid Cooperative Catalysis: Enantioselective Construction of Dihydropyridinones.异硫脲与布朗斯特酸协同催化:二氢吡啶酮的对映选择性构建
Org Lett. 2020 Mar 20;22(6):2261-2265. doi: 10.1021/acs.orglett.0c00461. Epub 2020 Mar 2.
2
Enantioselective Synthesis of α-Aryl-β -Amino-Esters by Cooperative Isothiourea and Brønsted Acid Catalysis.手性亚砜催化的α-芳基-β-氨基酯的对映选择性合成。
Angew Chem Int Ed Engl. 2021 May 17;60(21):11892-11900. doi: 10.1002/anie.202016220. Epub 2021 May 4.
3
Multiple roles of aryloxide leaving groups in enantioselective annulations employing α,β-unsaturated acyl ammonium catalysis.在采用α,β-不饱和酰基铵催化的对映选择性环化反应中芳氧基离去基团的多重作用
Chem Sci. 2018 May 4;9(21):4909-4918. doi: 10.1039/c8sc01324a. eCollection 2018 Jun 7.
4
Cooperative Palladium/Isothiourea Catalyzed Enantioselective Formal (3+2) Cycloaddition of Vinylcyclopropanes and α,β-Unsaturated Esters.钯/异硫脲协同催化乙烯基环丙烷与α,β-不饱和酯的对映选择性形式(3+2)环加成反应
Angew Chem Int Ed Engl. 2022 Jun 20;61(25):e202202621. doi: 10.1002/anie.202202621. Epub 2022 Apr 28.
5
Construction of Axially Chiral Compounds via Asymmetric Organocatalysis.通过不对称有机催化构建轴向手性化合物。
Acc Chem Res. 2018 Feb 20;51(2):534-547. doi: 10.1021/acs.accounts.7b00602. Epub 2018 Feb 8.
6
Asymmetric aerobic decarboxylative Povarov reactions of N-aryl α-amino acids with methylenephthalimidines via cooperative photoredox and chiral Brønsted acid catalysis.通过光氧化还原和手性布朗斯台德酸协同催化,N-芳基α-氨基酸与亚甲基邻苯二甲酰亚胺的不对称需氧脱羧 Povarov 反应。
Chem Commun (Camb). 2019 Oct 24;55(86):12916-12919. doi: 10.1039/c9cc07380a.
7
Highly Enantioselective Allylic C-H Alkylation of Terminal Olefins with Pyrazol-5-ones Enabled by Cooperative Catalysis of Palladium Complex and Brønsted Acid.钯配合物与布朗斯特酸协同催化实现末端烯烃的高对映选择性烯丙基 C-H 烷基化反应。
J Am Chem Soc. 2016 Nov 2;138(43):14354-14361. doi: 10.1021/jacs.6b08236. Epub 2016 Oct 21.
8
Isothiourea-catalysed enantioselective radical conjugate addition under batch and flow conditions.异硫脲催化的分批和流动条件下的对映选择性自由基共轭加成。
Chem Commun (Camb). 2022 Jun 28;58(52):7277-7280. doi: 10.1039/d2cc02432b.
9
NHC-Catalyzed Generation of α,β-Unsaturated Acylazoliums for the Enantioselective Synthesis of Heterocycles and Carbocycles.NHC 催化生成 α,β-不饱和酰基氮鎓盐用于杂环和碳环的对映选择性合成。
Acc Chem Res. 2019 Feb 19;52(2):425-436. doi: 10.1021/acs.accounts.8b00550. Epub 2019 Jan 17.
10
Unanticipated Silyl Transfer in Enantioselective α,β-Unsaturated Acyl Ammonium Catalysis Using Silyl Nitronates.使用硅基硝酸酯在对映选择性α,β-不饱和酰基铵催化中意外的硅基转移
Org Lett. 2020 Jan 3;22(1):335-339. doi: 10.1021/acs.orglett.9b04404. Epub 2019 Dec 23.

引用本文的文献

1
Chiral sulfide and achiral sulfonic acid cocatalyzed enantioselective electrophilic tandem selenylation semipinacol rearrangement of allenols.手性硫化物和非手性磺酸共催化烯丙醇的对映选择性亲电串联硒化半频哪醇重排反应
Nat Commun. 2025 Mar 3;16(1):2147. doi: 10.1038/s41467-025-57381-w.
2
Cooperative Palladium/Isothiourea Catalyzed Enantioselective Formal (3+2) Cycloaddition of Vinylcyclopropanes and α,β-Unsaturated Esters.钯/异硫脲协同催化乙烯基环丙烷与α,β-不饱和酯的对映选择性形式(3+2)环加成反应
Angew Chem Int Ed Engl. 2022 Jun 20;61(25):e202202621. doi: 10.1002/anie.202202621. Epub 2022 Apr 28.
3
Solvent directed chemically divergent synthesis of β-lactams and α-amino acid derivatives with chiral isothiourea.
溶剂导向的手性异硫脲介导的β-内酰胺和α-氨基酸衍生物的化学发散合成
Chem Sci. 2022 Jan 18;13(6):1801-1807. doi: 10.1039/d1sc06127e. eCollection 2022 Feb 9.
4
Enantioselective Synthesis of α-Aryl-β -Amino-Esters by Cooperative Isothiourea and Brønsted Acid Catalysis.手性亚砜催化的α-芳基-β-氨基酯的对映选择性合成。
Angew Chem Int Ed Engl. 2021 May 17;60(21):11892-11900. doi: 10.1002/anie.202016220. Epub 2021 May 4.