• 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2-羟基-1,4-萘醌与硝基烯烃的高度对映选择性迈克尔加成反应。

Organocatalytic highly enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes.

作者信息

Zhou Wen-Ming, Liu Han, Du Da-Ming

机构信息

Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing, PRC.

出版信息

Org Lett. 2008 Jul 3;10(13):2817-20. doi: 10.1021/ol800945e. Epub 2008 Jun 6.

DOI:10.1021/ol800945e
PMID:18533672
Abstract

The first organocatalytic enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes for the direct synthesis of chiral nitroalkylated naphthoquinone derivatives was investigated. Good yields and excellent enantioselectivities (up to >99% ee) could be achieved. This organocatalytic asymmetric Michael addition provides an efficient route toward the synthesis of optically active functionalized naphthoquinones.

摘要

研究了首例通过有机催化2-羟基-1,4-萘醌与硝基烯烃的对映选择性迈克尔加成反应直接合成手性硝基烷基化萘醌衍生物。该反应能获得良好的产率和优异的对映选择性(高达>99% ee)。这种有机催化的不对称迈克尔加成为合成光学活性官能化萘醌提供了一条有效途径。

相似文献

1
Organocatalytic highly enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes.有机催化2-羟基-1,4-萘醌与硝基烯烃的高度对映选择性迈克尔加成反应。
Org Lett. 2008 Jul 3;10(13):2817-20. doi: 10.1021/ol800945e. Epub 2008 Jun 6.
2
Urea- and thiourea-substituted cinchona alkaloid derivatives as highly efficient bifunctional organocatalysts for the asymmetric addition of malonate to nitroalkenes: inversion of configuration at C9 dramatically improves catalyst performance.尿素和硫脲取代的金鸡纳生物碱衍生物作为丙二酸酯对硝基烯烃不对称加成反应的高效双功能有机催化剂:C9位构型翻转显著提高催化剂性能。
Angew Chem Int Ed Engl. 2005 Oct 7;44(39):6367-70. doi: 10.1002/anie.200501721.
3
Organocatalytic sequential Michael reactions: stereoselective synthesis of multifunctionalized tetrahydroindan derivatives.有机催化串联 Michael 反应:多功能四氢茚衍生物的立体选择性合成。
Org Lett. 2011 Mar 4;13(5):936-9. doi: 10.1021/ol1029832. Epub 2011 Feb 10.
4
Enantioselective organocatalytic Michael addition reactions between N-heterocycles and nitroolefins.氮杂环与硝基烯烃之间的对映选择性有机催化迈克尔加成反应。
Org Lett. 2006 Mar 30;8(7):1391-4. doi: 10.1021/ol0601794.
5
Enantioselective organocatalytic direct Michael addition of nitroalkanes to nitroalkenes promoted by a unique bifunctional DMAP-thiourea.由独特的双功能 DMAP-硫脲促进的硝基烷烃对硝基烯烃的对映选择性有机催化直接迈克尔加成反应。
J Am Chem Soc. 2008 Oct 15;130(41):13524-5. doi: 10.1021/ja805390k. Epub 2008 Sep 23.
6
Asymmetric 1,4-addition of oxazolones to nitroalkenes by bifunctional cinchona alkaloid thiourea organocatalysts: synthesis of alpha,alpha-disubstituted alpha-amino acids.双功能金鸡纳生物碱硫脲有机催化剂催化噁唑酮对硝基烯烃的不对称1,4-加成反应:α,α-二取代α-氨基酸的合成
Chemistry. 2008;14(35):10958-66. doi: 10.1002/chem.200802030.
7
Organocatalytic asymmetric Michael addition of 2,4-pentandione to nitroolefins.2,4-戊二酮对硝基烯烃的有机催化不对称迈克尔加成反应。
Org Lett. 2005 Oct 13;7(21):4713-6. doi: 10.1021/ol0519137.
8
Organocatalytic enantioselective cascade Michael-Michael-Wittig reactions of phosphorus ylides: one-pot synthesis of the all-cis trisubstituted cyclohexenecarboxylates via the [1 + 2 + 3] annulation.有机催化对映选择性级联 Michael-Michael-Wittig 反应的磷叶立德:通过 [1 + 2 + 3] 环加成一锅法合成全顺式三取代环己烯羧酸酯。
Org Lett. 2009 Nov 19;11(22):5246-9. doi: 10.1021/ol9021832.
9
Asymmetric direct vinylogous Michael reaction of activated alkenes to nitroolefins catalyzed by modified cinchona alkaloids.修饰金鸡纳生物碱催化的活性烯烃与硝基烯烃的不对称直接乙烯型迈克尔反应。
Org Lett. 2005 Nov 10;7(23):5293-6. doi: 10.1021/ol052283b.
10
Direct asymmetric Michael addition of thioether-based aryl sulfanyl-propan-2-one to nitroalkenes catalyzed by a chiral amine-thiourea bifunctional organocatalyst.手性伯胺-硫脲双功能有机催化剂催化硫醚基芳基硫基-2-丙酮与硝基烯烃的直接不对称迈克尔加成反应。
Chirality. 2010 Jul;22(7):625-34. doi: 10.1002/chir.20689.

引用本文的文献

1
Biodegradation of 2-hydroxyl-1,4 naphthoquinone (lawsone) by Pseudomonas taiwanensis LH-3 isolated from activated sludge.从活性污泥中分离出的假单胞菌 LH-3 对 2-羟基-1,4 萘醌(龙葵素)的生物降解作用。
Sci Rep. 2017 Jul 28;7(1):6795. doi: 10.1038/s41598-017-06338-1.
2
New hydrogen-bonding organocatalysts: Chiral cyclophosphazanes and phosphorus amides as catalysts for asymmetric Michael additions.新型氢键有机催化剂:手性环磷酰胺和磷酰胺作为不对称迈克尔加成反应的催化剂。
Beilstein J Org Chem. 2014 Jan 21;10:224-36. doi: 10.3762/bjoc.10.18. eCollection 2014.
3
Enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes catalyzed by binaphthyl-derived organocatalysts.
手性双萘酚衍生有机催化剂催化的 2-羟基-1,4-萘醌对硝基烯烃的对映选择性迈克尔加成反应。
Beilstein J Org Chem. 2012;8:699-704. doi: 10.3762/bjoc.8.78. Epub 2012 May 7.
4
Ethyl (2S,4R)-4-(4-bromo-phen-yl)-2-hydr-oxy-5,10-dioxo-3,4,5,10-tetra-hydro-2H-benzo[g]chromene-2-carboxyl-ate.(2S,4R)-4-(4-溴苯基)-2-羟基-5,10-二氧代-3,4,5,10-四氢-2H-苯并[g]色烯-2-羧酸乙酯
Acta Crystallogr Sect E Struct Rep Online. 2010 Jan 16;66(Pt 2):o388. doi: 10.1107/S1600536810001315.