• 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

手性伯胺-水杨酰胺有机催化酮与马来酰亚胺的不对称共轭加成。

Asymmetric Conjugate Addition of Ketones to Maleimides Organocatalyzed by a Chiral Primary Amine-Salicylamide.

机构信息

Department of Organic Chemistry, Faculty of Sciences, Institute of Organic Synthesis (ISO), University of Alicante, Apdo. 99, 03080 Alicante, Spain.

出版信息

Molecules. 2022 Oct 7;27(19):6668. doi: 10.3390/molecules27196668.

DOI:10.3390/molecules27196668
PMID:36235205
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9573004/
Abstract

Enantioenriched substituted succinimides are interesting compounds, and their asymmetric organocatalytic synthesis by the conjugated addition of ketones to maleimides has been scarcely explored. This study shows the enantioselective conjugate addition of ketones to maleimides organocatalyzed by a simple primary amine-salicylamide derived from a chiral -cyclohexane-1,2-diamine, which provides the desired succinimides in good to excellent yields (up to 98%) and with moderate to excellent enantioselectivities (up to 99%).

摘要

对映富集取代琥珀酰亚胺是一类有趣的化合物,其通过酮与马来酰亚胺的共轭加成进行不对称有机催化合成的研究还很少。本研究展示了一种简单的手性 -环己烷-1,2-二胺衍生的伯胺-水杨酰胺对酮与马来酰亚胺的对映选择性共轭加成的有机催化作用,该方法提供了所需的琥珀酰亚胺,产率高(高达 98%),对映选择性适中至优异(高达 99%)。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f10c/9573004/b3bec84fc827/molecules-27-06668-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f10c/9573004/6f42a76097b7/molecules-27-06668-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f10c/9573004/7d50058945d2/molecules-27-06668-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f10c/9573004/c0ddaa3ba23f/molecules-27-06668-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f10c/9573004/b3bec84fc827/molecules-27-06668-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f10c/9573004/6f42a76097b7/molecules-27-06668-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f10c/9573004/7d50058945d2/molecules-27-06668-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f10c/9573004/c0ddaa3ba23f/molecules-27-06668-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f10c/9573004/b3bec84fc827/molecules-27-06668-g004.jpg

相似文献

1
Asymmetric Conjugate Addition of Ketones to Maleimides Organocatalyzed by a Chiral Primary Amine-Salicylamide.手性伯胺-水杨酰胺有机催化酮与马来酰亚胺的不对称共轭加成。
Molecules. 2022 Oct 7;27(19):6668. doi: 10.3390/molecules27196668.
2
Enantioselective Michael Addition of Aldehydes to Maleimides Organocatalyzed by a Chiral Primary Amine-Salicylamide.手性伯胺-水杨酰胺催化的醛与马来酰亚胺的对映选择性迈克尔加成。
Molecules. 2018 Dec 12;23(12):3299. doi: 10.3390/molecules23123299.
3
Organocatalytic Asymmetric Conjugate Addition of Aldehydes to Maleimides and Nitroalkenes in Deep Eutectic Solvents.有机催化醛与马来酰亚胺和硝基亚乙烯在深共晶溶剂中的不对称共轭加成。
Molecules. 2019 Nov 9;24(22):4058. doi: 10.3390/molecules24224058.
4
Asymmetric Conjugate Addition of α,α-Disubstituted Aldehydes to Nitroalkenes Organocatalyzed by Chiral Monosalicylamides from trans-Cyclohexane-1,2-Diamines.手性单水杨酰胺催化的反式-1,2-环己二胺衍生的亚砜诱导的α,α-二取代醛与硝基烯烃的不对称共轭加成。
Molecules. 2018 Jan 11;23(1):141. doi: 10.3390/molecules23010141.
5
Chiral Primary Amine Catalyzed α-Arylation of Simple Ketones via Asymmetric Retro-Claisen Cleavage.手性伯胺催化简单酮的不对称[1,5]-芳基迁移重排反应。
Chemistry. 2022 Dec 20;28(71):e202202584. doi: 10.1002/chem.202202584. Epub 2022 Oct 27.
6
Role of Cinchona Alkaloids in the Enantio- and Diastereoselective Synthesis of Axially Chiral Compounds.金鸡纳生物碱在手性轴和非对映选择性合成中的作用。
Acc Chem Res. 2022 Dec 20;55(24):3551-3571. doi: 10.1021/acs.accounts.2c00515. Epub 2022 Dec 7.
7
Enantioselective Michael addition of ketones to maleimides catalyzed by bifunctional monosulfonyl DPEN salt.手性双功能单磺酰基 DPEN 盐催化的酮对马来酰亚胺的对映选择性迈克尔加成。
Chem Commun (Camb). 2010 Jul 7;46(25):4589-91. doi: 10.1039/c0cc00774a. Epub 2010 May 18.
8
Direct synthesis of chiral 3-arylsuccinimides by rhodium-catalyzed enantioselective conjugate addition of arylboronic acids to maleimides.通过铑催化芳基硼酸对马来酰亚胺的对映选择性共轭加成直接合成手性3-芳基琥珀酰亚胺。
Chemistry. 2015 Jul 27;21(31):11050-5. doi: 10.1002/chem.201501059. Epub 2015 Jun 3.
9
Asymmetric sulfa-Michael addition to α-substituted vinyl ketones catalyzed by chiral primary amine.手性伯胺催化的α-取代乙烯基酮的不对称砜-迈克尔加成反应。
Org Lett. 2014 Sep 5;16(17):4626-9. doi: 10.1021/ol5022178. Epub 2014 Aug 21.
10
Enantioselective conjugate addition of both aromatic ketones and acetone to nitroolefins catalyzed by chiral primary amines bearing multiple hydrogen-bonding donors.手性伯胺多氢键给体催化芳香酮和丙酮与硝基烯烃的对映选择性共轭加成。
J Org Chem. 2012 Apr 20;77(8):4103-10. doi: 10.1021/jo300011x. Epub 2012 Mar 29.

引用本文的文献

1
Diverse reactivity of maleimides in polymer science and beyond.马来酰亚胺在高分子科学及其他领域的多样反应性。
Polym Int. 2025 Apr;74(4):296-306. doi: 10.1002/pi.6715. Epub 2024 Nov 5.
2
Redox-active molecules as organocatalysts for selective oxidative transformations - an unperceived organocatalysis field.氧化还原活性分子作为用于选择性氧化转化的有机催化剂——一个未被察觉的有机催化领域。
Beilstein J Org Chem. 2022 Dec 9;18:1672-1695. doi: 10.3762/bjoc.18.179. eCollection 2022.

本文引用的文献

1
N-Primary-amine tetrapeptide-catalyzed highly asymmetric Michael addition of aliphatic aldehydes to maleimides.N-伯胺四肽催化脂肪醛与马来酰亚胺的高度不对称迈克尔加成反应。
Org Biomol Chem. 2020 Sep 21;18(35):6899-6904. doi: 10.1039/d0ob01457e. Epub 2020 Aug 28.
2
Design, synthesis, in-vitro, in-vivo and in-silico studies of pyrrolidine-2,5-dione derivatives as multitarget anti-inflammatory agents.吡咯烷-2,5-二酮衍生物作为多靶点抗炎剂的设计、合成、体外、体内和计算机研究。
Eur J Med Chem. 2020 Jan 15;186:111863. doi: 10.1016/j.ejmech.2019.111863. Epub 2019 Nov 10.
3
Organocatalytic Asymmetric Conjugate Addition of Aldehydes to Maleimides and Nitroalkenes in Deep Eutectic Solvents.
有机催化醛与马来酰亚胺和硝基亚乙烯在深共晶溶剂中的不对称共轭加成。
Molecules. 2019 Nov 9;24(22):4058. doi: 10.3390/molecules24224058.
4
Enantioselective Michael Addition of Aldehydes to Maleimides Organocatalyzed by a Chiral Primary Amine-Salicylamide.手性伯胺-水杨酰胺催化的醛与马来酰亚胺的对映选择性迈克尔加成。
Molecules. 2018 Dec 12;23(12):3299. doi: 10.3390/molecules23123299.
5
Solvent-Free Enantioselective Michael Reactions Catalyzed by a Calixarene-Based Primary Amine Thiourea.基于杯芳烃的伯胺硫脲催化的无溶剂对映选择性迈克尔反应
J Org Chem. 2018 Sep 7;83(17):10318-10325. doi: 10.1021/acs.joc.8b01454. Epub 2018 Jul 11.
6
Asymmetric Michael Addition Organocatalyzed by α,β-Dipeptides under Solvent-Free Reaction Conditions.无溶剂反应条件下 α,β-二肽催化不对称 Michael 加成反应。
Molecules. 2017 Aug 10;22(8):1328. doi: 10.3390/molecules22081328.
7
Highly enantioselective Michael addition promoted by a new diterpene-derived bifunctional thiourea catalyst: a doubly stereocontrolled approach to chiral succinimide derivatives.一种新型二萜衍生双功能硫脲催化剂促进的高度对映选择性迈克尔加成反应:一种构建手性琥珀酰亚胺衍生物的双重立体控制方法。
Chirality. 2014 Feb;26(2):121-7. doi: 10.1002/chir.22279. Epub 2014 Jan 14.
8
An asymmetric Michael addition of α,α-disubstituted aldehydes to maleimides leading to a one-pot enantioselective synthesis of lactones catalyzed by amino acids.氨基酸催化的α,α-二取代醛与马来酰亚胺的不对称迈克尔加成反应一锅法高效对映选择性合成内酯。
Org Lett. 2013 May 17;15(10):2406-9. doi: 10.1021/ol4008662. Epub 2013 Apr 29.
9
Molecular assembly of an achiral phosphine and a chiral primary amine: a highly efficient supramolecular catalyst for the enantioselective Michael reaction of aldehydes with maleimides.手性伯胺与非手性膦的分子组装:一种高效的超分子催化剂,用于醛与马来酰亚胺的对映选择性迈克尔加成反应。
Chem Asian J. 2013 Jun;8(6):1182-90. doi: 10.1002/asia.201300141. Epub 2013 Apr 3.
10
Automated three-component synthesis of a library of γ-lactams.自动化三组分合成γ-内酰胺文库。
Beilstein J Org Chem. 2012;8:1804-13. doi: 10.3762/bjoc.8.206. Epub 2012 Oct 19.