• 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

有机催化不对称硫醇与α,β-不饱和全氟异丙酯的磺酰迈克尔加成反应:快速获得 (R)-噻唑嗪。

Organocatalytic asymmetric sulfa-Michael addition of thiols to α,β-unsaturated hexafluoroisopropyl esters: expeditious access to (R)-thiazesim.

机构信息

College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072, China.

出版信息

Org Lett. 2013 Jul 5;15(13):3448-51. doi: 10.1021/ol4015305. Epub 2013 Jun 17.

DOI:10.1021/ol4015305
PMID:23772965
Abstract

A highly efficient organocatalytic asymmetric SMA reaction of hexafluoroisopropyl α,β-unsaturated esters has been developed. Introducing electron-withdrawing hexafluoroisopropyl ester is crucial to enhancing the electrophilicity of unsaturated esters as SMA acceptors. The catalytic system performs well over a broad scope of α,β-unsaturated esters and diversified thiols and provides facile access to (R)-thiazesim in a one-pot protocol.

摘要

已开发出一种高效的手性有机催化不对称 SMA 反应,用于六氟异丙基α,β-不饱和酯。引入吸电子的六氟异丙基酯对于增强不饱和酯作为 SMA 受体的亲电性至关重要。该催化体系在广泛的α,β-不饱和酯和各种硫醇的范围内表现良好,并提供了一种在一锅法中方便地合成(R)-噻唑啉的方法。

相似文献

1
Organocatalytic asymmetric sulfa-Michael addition of thiols to α,β-unsaturated hexafluoroisopropyl esters: expeditious access to (R)-thiazesim.有机催化不对称硫醇与α,β-不饱和全氟异丙酯的磺酰迈克尔加成反应:快速获得 (R)-噻唑嗪。
Org Lett. 2013 Jul 5;15(13):3448-51. doi: 10.1021/ol4015305. Epub 2013 Jun 17.
2
Catalytic asymmetric conjugate addition of thiols to α,β-unsaturated thioamides: expeditious access to enantioenriched 1,5-benzothiazepines.手性催化硫醇与α,β-不饱和硫代酰胺的共轭加成反应:快速构建手性富集的 1,5-苯并硫氮杂卓。
Angew Chem Int Ed Engl. 2012 Aug 20;51(34):8551-4. doi: 10.1002/anie.201204365. Epub 2012 Jul 16.
3
Chiral squaramide-catalysed one-pot enantioselective sulfa-Michael addition/thioesterification of thiols with α,β-unsaturated N-acylated succinimides.手性螺噁嗪催化一锅法对映选择性硫代迈克尔加成/硫酯化反应,用于α,β-不饱和 N-酰化琥珀酰亚胺与硫醇的反应。
Org Biomol Chem. 2014 Mar 14;12(10):1585-94. doi: 10.1039/c3ob42137f.
4
Organocatalytic asymmetric sulfa-Michael addition of thiols to 4,4,4-trifluorocrotonates.有机催化不对称磺酸迈克尔加成反应硫醇对 4,4,4-三氟巴豆酸酯。
Org Lett. 2011 Aug 19;13(16):4426-9. doi: 10.1021/ol201766k. Epub 2011 Jul 26.
5
Enantioselective Synthesis of N-H-Free 1,5-Benzothiazepines.无N-H的1,5-苯并硫氮杂䓬的对映选择性合成。
Chemistry. 2017 Jan 12;23(3):554-557. doi: 10.1002/chem.201605127. Epub 2016 Nov 29.
6
Catalytic asymmetric 1,4-addition reactions using alpha,beta-unsaturated N-acylpyrroles as highly reactive monodentate alpha,beta-unsaturated ester surrogates.使用α,β-不饱和N-酰基吡咯作为高反应性单齿α,β-不饱和酯替代物的催化不对称1,4-加成反应。
J Am Chem Soc. 2004 Jun 23;126(24):7559-70. doi: 10.1021/ja0485917.
7
Asymmetric Organocatalytic Sulfa-Michael Addition to Enone Diesters.不对称有机催化磺酸-迈克尔加成到烯酮二酯。
J Org Chem. 2018 Mar 16;83(6):3385-3391. doi: 10.1021/acs.joc.8b00007. Epub 2018 Mar 7.
8
Organocatalytic asymmetric aldol reaction of hydroxyacetone with β,γ-unsaturated α-keto esters: facile access to chiral tertiary alcohols.有机催化不对称羟醛缩合反应:β,γ-不饱和α-酮酯与羟基丙酮的反应:手性叔醇的简便合成方法。
Org Lett. 2011 Oct 7;13(19):5248-51. doi: 10.1021/ol2021274. Epub 2011 Sep 8.
9
Highly efficient asymmetric synthesis of α,β-epoxy esters via one-pot organocatalytic epoxidation and oxidative esterification.通过一锅相有机催化环氧化和氧化酯化反应,高效不对称合成α,β-环氧酯。
Org Biomol Chem. 2013 Mar 21;11(11):1815-7. doi: 10.1039/c3ob00056g. Epub 2013 Feb 8.
10
Highly enantioselective Cu(I)-Tol-BINAP-catalyzed asymmetric conjugate addition of Grignard reagents to α,β-unsaturated esters.高对映选择性的 Cu(I)-Tol-BINAP 催化的格氏试剂对α,β-不饱和酯的不对称共轭加成。
Chem Commun (Camb). 2010 Dec 14;46(46):8694-703. doi: 10.1039/c0cc03211e. Epub 2010 Oct 29.

引用本文的文献

1
Synthesis of carbonyl-functionalized mercaptosilsesquioxane.羰基官能化巯基硅倍半氧烷的合成
Sci Rep. 2025 Aug 11;15(1):29286. doi: 10.1038/s41598-025-14360-x.
2
One-Pot NIS-Promoted Cyclization/Palladium-Catalyzed Carbonylation for the Selective Synthesis of HFIP Ester-Containing Indenes and Thiochromenes.一锅法NIS促进的环化/钯催化的羰基化反应用于选择性合成含HFIP酯的茚和硫代色烯。
ACS Org Inorg Au. 2025 Feb 21;5(2):156-163. doi: 10.1021/acsorginorgau.5c00005. eCollection 2025 Apr 2.
3
Eco-Friendly Functionalization of Ynals with Thiols under Mild Conditions.
在温和条件下用硫醇对 Ynals 进行环保功能化。
Int J Mol Sci. 2024 Aug 24;25(17):9201. doi: 10.3390/ijms25179201.
4
Electronic Effects in a Green Protocol for (Hetero)Aryl-S Coupling.用于(杂)芳基-S偶联的绿色方案中的电子效应
Molecules. 2024 Apr 10;29(8):1714. doi: 10.3390/molecules29081714.
5
Scale-up of Sodium Persulfate Mediated, Nitroxide Catalyzed Oxidative Functionalization Reactions.过硫酸钠介导、氮氧化物催化的氧化官能团化反应的放大
Curr Org Synth. 2024;21(7):941-946. doi: 10.2174/1570179421666230831105337.
6
Progress on the Cu-Catalyzed 1,4-Conjugate Addition to Thiochromones.铜催化硫代色酮的1,4-共轭加成反应研究进展
Catalysts. 2023 Apr;13(4). doi: 10.3390/catal13040713. Epub 2023 Apr 8.
7
The synthesis of chiral β-naphthyl-β-sulfanyl ketones via enantioselective sulfa-Michael reaction in the presence of a bifunctional cinchona/sulfonamide organocatalyst.在双功能金鸡纳碱/磺酰胺有机催化剂存在下,通过对映选择性硫醇-迈克尔反应合成手性β-萘基-β-硫烷基酮。
Beilstein J Org Chem. 2021 Feb 18;17:494-503. doi: 10.3762/bjoc.17.43. eCollection 2021.
8
A solvent-dependent chirality-switchable thia-Michael addition to α,β-unsaturated carboxylic acids using a chiral multifunctional thiourea catalyst.使用手性多功能硫脲催化剂对α,β-不饱和羧酸进行溶剂依赖性手性可切换硫杂迈克尔加成反应。
Chem Sci. 2020 May 14;11(21):5572-5576. doi: 10.1039/d0sc01729a. eCollection 2020 Jun 7.
9
Conjugate Addition of Grignard Reagents to Thiochromones Catalyzed by Copper Salts: A Unified Approach to Both 2-Alkylthiochroman-4-One and Thioflavanone.铜盐催化的硫代色酮与格氏试剂的共轭加成:2-烷基硫代色满-4-酮和硫色满酮的统一方法。
Molecules. 2020 May 1;25(9):2128. doi: 10.3390/molecules25092128.
10
Efficient Synthesis of 1,4-Thiazepanones and 1,4-Thiazepanes as 3D Fragments for Screening Libraries.高效合成 1,4-噻嗪酮和 1,4-噻嗪烷作为 3D 片段用于筛选库。
Org Lett. 2020 May 15;22(10):3946-3950. doi: 10.1021/acs.orglett.0c01230. Epub 2020 Apr 29.