• 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

高压条件下丙二酸二烷基酯对β-芳基乙烯基磺酰氟的对映选择性加成反应

Enantioselective Addition of Dialkyl Malonates to β-Arylethenesulfonyl Fluorides under High-Pressure Conditions.

作者信息

Kopyt Michał, Tryniszewski Michał, Barbasiewicz Michał, Kwiatkowski Piotr

机构信息

Faculty of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland.

Biological and Chemical Research Centre, University of Warsaw, Żwirki i Wigury 101, 02-089 Warsaw, Poland.

出版信息

Org Lett. 2023 Sep 22;25(37):6818-6822. doi: 10.1021/acs.orglett.3c02302. Epub 2023 Sep 1.

DOI:10.1021/acs.orglett.3c02302
PMID:37655810
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10521026/
Abstract

Application of high-pressure conditions enables enantioselective Michael-type addition of dialkyl malonates to β-arylethenesulfonyl fluorides. The reaction is efficiently catalyzed with 5 mol % of tertiary amino-thiourea at 9 kbar. Chiral alkanesulfonyl fluorides are formed in yields of up to 96% and enantioselectivities of up to 92%. Functionalization of the adducts via sulfur fluoride exchange (SuFEx) reaction and desulfonylative cyclization is demonstrated.

摘要

高压条件的应用能够实现丙二酸二烷基酯对β-芳基乙烯基磺酰氟的对映选择性迈克尔型加成反应。该反应在9千巴压力下用5摩尔%的叔氨基硫脲能高效催化。手性链烷磺酰氟的产率高达96%，对映选择性高达92%。还展示了通过硫氟交换（SuFEx）反应和脱磺酰环化对加合物进行官能团化。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d1e1/10521026/ed912737926c/ol3c02302_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d1e1/10521026/b52e1a71decb/ol3c02302_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d1e1/10521026/a4080cb5258c/ol3c02302_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d1e1/10521026/f9608530c6f5/ol3c02302_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d1e1/10521026/3745f25e976a/ol3c02302_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d1e1/10521026/ed912737926c/ol3c02302_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d1e1/10521026/b52e1a71decb/ol3c02302_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d1e1/10521026/a4080cb5258c/ol3c02302_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d1e1/10521026/f9608530c6f5/ol3c02302_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d1e1/10521026/3745f25e976a/ol3c02302_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d1e1/10521026/ed912737926c/ol3c02302_0005.jpg

相似文献

1
Enantioselective Addition of Dialkyl Malonates to β-Arylethenesulfonyl Fluorides under High-Pressure Conditions.高压条件下丙二酸二烷基酯对β-芳基乙烯基磺酰氟的对映选择性加成反应
Org Lett. 2023 Sep 22;25(37):6818-6822. doi: 10.1021/acs.orglett.3c02302. Epub 2023 Sep 1.
2
A Heck-Matsuda Process for the Synthesis of β-Arylethenesulfonyl Fluorides: Selectively Addressable Bis-electrophiles for SuFEx Click Chemistry.一种 Heck-Matsuda 反应合成β-芳基乙烯砜氟化物的方法：用于 SuFEx 点击化学的选择性可寻址双亲电试剂。
Angew Chem Int Ed Engl. 2016 Nov 2;55(45):14155-14158. doi: 10.1002/anie.201608807. Epub 2016 Oct 10.
3
Enantioselective Michael reaction of malonates to nitroolefins catalyzed by bifunctional organocatalysts.双功能有机催化剂催化丙二酸酯与硝基烯烃的对映选择性迈克尔反应。
J Am Chem Soc. 2003 Oct 22;125(42):12672-3. doi: 10.1021/ja036972z.
4
An efficient organocatalytic method for highly enantioselective Michael addition of malonates to enones catalyzed by readily accessible primary amine-thiourea.一种高效的手性有机催化方法，通过易于获得的伯胺-硫脲催化丙二酸酯对烯酮的高对映选择性迈克尔加成。
Org Lett. 2012 Aug 17;14(16):4222-5. doi: 10.1021/ol3019055. Epub 2012 Aug 9.
5
Organocatalyzed enantioselective Michael addition/cyclization cascade reaction of 3-isothiocyanato oxindoles with arylidene malonates.3-异硫氰酸酯氧化吲哚与亚芳基丙二酸酯的有机催化对映选择性迈克尔加成/环化串联反应
Org Biomol Chem. 2016 Nov 29;14(47):11250-11260. doi: 10.1039/c6ob02104b.
6
Enantioselective organocatalytic michael addition of malonates to alpha,beta-unsaturated ketones.丙二酸酯对α,β-不饱和酮的对映选择性有机催化迈克尔加成反应。
Org Lett. 2009 Feb 5;11(3):753-6. doi: 10.1021/ol802892h.
7
Synthesis of α-Bromo Arylethyl Sulfonyl Fluorides and β-Arylethenesulfonyl Fluorides via Copper-Catalyzed Meerwein Arylation.通过铜催化的迈尔温芳基化反应合成α-溴芳基乙基磺酰氟和β-芳基乙烯基磺酰氟
J Org Chem. 2024 Sep 20;89(18):13709-13718. doi: 10.1021/acs.joc.4c01002. Epub 2024 Aug 16.
8
Lithium Binaphtholate-Catalyzed Michael Reaction of Malonates with Maleates and Its Application to the Enantioselective Synthesis of Tricarboxylic Acid Derivatives.联萘酚锂催化丙二酸酯与马来酸酯的迈克尔反应及其在三羧酸衍生物对映选择性合成中的应用
Chem Pharm Bull (Tokyo). 2019;67(5):452-460. doi: 10.1248/cpb.c18-00993.
9
β-Aminosulfonyl Fluorides via Water-Accelerated N-Heterocyclic Carbene Catalysis.β-氨磺酰氟化物的水相加速 N-杂环卡宾催化合成。
ChemSusChem. 2022 Sep 20;15(18):e202201000. doi: 10.1002/cssc.202201000. Epub 2022 Jul 27.
10
Enantioselective and regioselective organocatalytic conjugate addition of malonates to nitroenynes.手性和区域选择性的有机催化丙二酸酯与硝基烯炔的共轭加成反应。
Chem Asian J. 2011 Jan 3;6(1):220-5. doi: 10.1002/asia.201000561.

引用本文的文献

1
Enantioselective Organocatalytic Addition of 1,3-Dicarbonyl Compounds to β-Arylvinyl Triflones.1,3 - 二羰基化合物对β - 芳基乙烯基三氟甲磺酸酯的对映选择性有机催化加成反应
Org Lett. 2025 Mar 28;27(12):2879-2884. doi: 10.1021/acs.orglett.5c00412. Epub 2025 Mar 19.
2
Computational Identification of Potential Organocatalysts (CIPOC) Reveals a 2-aminoDMAP/Urea Catalyst Superior to Its Thiourea Analogue.潜在有机催化剂的计算识别（CIPOC）揭示了一种优于其硫脲类似物的2-氨基DMAP/尿素催化剂。
J Am Chem Soc. 2025 Mar 26;147(12):10078-10087. doi: 10.1021/jacs.4c10634. Epub 2025 Mar 11.

本文引用的文献

1
Sulfonyl fluorides as targets and substrates in the development of new synthetic methods.磺酰氟作为新型合成方法发展中的目标和底物。
Nat Rev Chem. 2022 Feb;6(2):146-162. doi: 10.1038/s41570-021-00352-8. Epub 2022 Jan 19.
2
Alkyl Sulfonyl Fluorides Incorporating Geminal Dithioesters as SuFEx Click Hubs via Water-Accelerated Organosuperbase Catalysis.通过水加速有机超强碱催化，将包含偕二硫代酯的烷基磺酰氟作为 SuFEx 点击枢纽进行烷基化。
Org Lett. 2023 Feb 24;25(7):1056-1060. doi: 10.1021/acs.orglett.2c04224. Epub 2023 Feb 10.
3
Chemical and biology of sulfur fluoride exchange (SuFEx) click chemistry for drug discovery.
硫氟交换（SuFEx）点击化学的化学和生物学在药物发现中的应用。
Bioorg Chem. 2023 Jan;130:106227. doi: 10.1016/j.bioorg.2022.106227. Epub 2022 Oct 30.
4
Olefination with Sulfonyl Halides and Esters: Synthesis of Unsaturated Sulfonyl Fluorides.用磺酰卤和酯进行烯化反应：不饱和磺酰氟的合成。
Org Lett. 2022 Jun 17;24(23):4270-4274. doi: 10.1021/acs.orglett.2c01604. Epub 2022 Jun 2.
5
Hydrophobic Amplification Enabled High-Turnover Phosphazene Superbase Catalysis.水相放大促进高转化率磷氮超碱催化。
ChemSusChem. 2022 Aug 5;15(15):e202200634. doi: 10.1002/cssc.202200634. Epub 2022 Jun 22.
6
Amino-oxetanes as amide isosteres by an alternative defluorosulfonylative coupling of sulfonyl fluorides.通过对磺酰氟的另一种脱氟磺酰化偶联反应，将氨基噁唑烷用作酰胺等排物。
Nat Chem. 2022 Feb;14(2):160-169. doi: 10.1038/s41557-021-00856-2. Epub 2022 Jan 27.
7
Highly Enantioselective Addition of -2,2,2-Trifluoroethylisatin Ketimines to Ethylene Sulfonyl Fluoride.高度对映选择性地将-2,2,2-三氟乙亚胺酮与乙烯砜氟加成。
J Org Chem. 2021 Feb 5;86(3):3041-3048. doi: 10.1021/acs.joc.0c02511. Epub 2021 Jan 27.
8
Rh-Catalyzed Highly Enantioselective Synthesis of Aliphatic Sulfonyl Fluorides.铑催化的脂肪族磺酰氟的高度对映选择性合成
iScience. 2019 Nov 22;21:695-705. doi: 10.1016/j.isci.2019.10.051. Epub 2019 Oct 30.
9
Metal-Free Synthesis of Functional 1-Substituted-1,2,3-Triazoles from Ethenesulfonyl Fluoride and Organic Azides.由乙烯基磺酰氟和有机叠氮化物无金属合成功能性1-取代-1,2,3-三唑
Angew Chem Int Ed Engl. 2020 Jan 13;59(3):1181-1186. doi: 10.1002/anie.201912728. Epub 2019 Nov 28.
10
Asymmetric synthesis of cyclopentanones through dual Lewis acid-catalysed [3+2]-cycloaddition of donor-acceptor cyclopropanes with ketenes.通过双路易斯酸催化的给体-受体环丙烷与烯酮的[3+2]-环加成反应，不对称合成环戊酮。
Chem Commun (Camb). 2019 Nov 7;55(90):13558-13561. doi: 10.1039/c9cc07477e.