• 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

双功能 3,3'-Ph2-BINOL-Mg 催化的α,β-不饱和γ-丁内酯的直接不对称烯醇式迈克尔加成反应。

Bifunctional 3,3'-Ph2-BINOL-Mg catalyzed direct asymmetric vinylogous Michael addition of α,β-unsaturated γ-butyrolactam.

机构信息

Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Institute of Biochemistry and Molecular Biology, Lanzhou University, Lanzhou, 730000, P. R. China.

出版信息

Org Lett. 2011 Dec 16;13(24):6410-3. doi: 10.1021/ol202713f. Epub 2011 Nov 16.

DOI:10.1021/ol202713f
PMID:22087591
Abstract

Bifunctional 3,3'-Ph(2)-BINOL-Mg catalyzed direct asymmetric vinylogous Michael addition of α,β-unsaturated γ-butyrolactam has been developed. The catalytic activity of this protocol was slightly affected by different types of Michael acceptors, such as a variety of enones as well as α,β-unsaturated N-acylpyrroles. The Michael products were obtained with high diastereoselectivities (up to 20:1) and excellent enantioselectivities (up to 98%).

摘要

双功能 3,3'-Ph(2)-BINOL-Mg 催化的 α,β-不饱和 γ-丁内酯的直接不对称烯醇式迈克尔加成已被开发出来。该反应方案的催化活性受不同类型的迈克尔受体的影响较小,如各种烯酮以及α,β-不饱和 N-酰基吡咯。迈克尔加成产物具有很高的非对映选择性(高达 20:1)和对映选择性(高达 98%)。

相似文献

1
Bifunctional 3,3'-Ph2-BINOL-Mg catalyzed direct asymmetric vinylogous Michael addition of α,β-unsaturated γ-butyrolactam.双功能 3,3'-Ph2-BINOL-Mg 催化的α,β-不饱和γ-丁内酯的直接不对称烯醇式迈克尔加成反应。
Org Lett. 2011 Dec 16;13(24):6410-3. doi: 10.1021/ol202713f. Epub 2011 Nov 16.
2
Organocatalytic direct asymmetric vinylogous Michael reaction of an α,β-unsaturated γ-butyrolactam with enones.有机催化的α,β-不饱和γ-丁内酰胺与烯酮的直接不对称 vinylogous Michael 反应。
J Org Chem. 2011 Mar 4;76(5):1472-4. doi: 10.1021/jo102223v. Epub 2011 Jan 18.
3
Asymmetric vinylogous Michael reaction of alpha,beta-unsaturated ketones with gamma-butenolide under multifunctional catalysis.在多功能催化作用下,α,β-不饱和酮与γ-丁内酯的不对称乙烯基迈克尔加成反应。
Chem Commun (Camb). 2010 Aug 28;46(32):5957-9. doi: 10.1039/c0cc01054e. Epub 2010 Jul 2.
4
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.
5
Organocatalyzed asymmetric vinylogous Michael addition of α,β-unsaturated γ-butyrolactam.有机催化的α,β-不饱和γ-丁内酯的不对称 vinylogous Michael 加成反应。
Chem Commun (Camb). 2013 Oct 18;49(81):9329-31. doi: 10.1039/c3cc44059a.
6
Efficient direct asymmetric vinylogous Michael addition reactions of gamma-butenolides to chalcones catalyzed by vicinal primary-diamine salts.手性邻二胺盐催化γ-丁烯内酯与查尔酮的高效不对称烯丙基迈克尔加成反应。
Chem Commun (Camb). 2010 Mar 28;46(12):2124-6. doi: 10.1039/b923925a. Epub 2010 Feb 19.
7
Zinc-mediated asymmetric additions of dialkylphosphine oxides to α,β-unsaturated ketones and N-sulfinylimines.锌介导的二烷基膦氧化物对α,β-不饱和酮和 N-亚磺酰亚胺的不对称加成反应。
J Org Chem. 2010 Oct 15;75(20):6756-63. doi: 10.1021/jo1014917.
8
Highly enantioselective Michael addition of malonates to beta,gamma-unsaturated alpha-ketoesters catalyzed by chiral N,N'-dioxide-Yttrium(III) complexes with convenient procedure.手性 N,N'-二氧化物-钇(III)配合物催化的丙二酸酯与β,γ-不饱和α-酮酯的高对映选择性迈克尔加成,具有方便的反应步骤。
Chem Commun (Camb). 2010 May 28;46(20):3601-3. doi: 10.1039/c002208j. Epub 2010 Apr 8.
9
Enantioselective Michael reaction of α-alkyl-β-keto esters and enones under multifunctional catalysis.手性迈克尔反应的 α-烷基-β-酮酯和烯酮在多功能催化下。
Org Lett. 2010 Nov 19;12(22):5218-21. doi: 10.1021/ol102256v. Epub 2010 Oct 18.
10
Direct catalytic asymmetric vinylogous Mannich-type and Michael reactions of an alpha,beta-unsaturated gamma-butyrolactam under dinuclear nickel catalysis.双核镍催化下,α,β-不饱和γ-丁内酰胺的直接不对称乙烯基曼尼希型和迈克尔反应。
J Am Chem Soc. 2010 Mar 24;132(11):3666-7. doi: 10.1021/ja1002636.

引用本文的文献

1
Regioselective α-addition of vinylogous α-ketoester enolate in organocatalytic asymmetric Michael reactions: enantioselective synthesis of Rauhut-Currier type products.有机催化不对称迈克尔反应中烯醇型α-酮酯烯醇盐的区域选择性α-加成:劳胡特-柯里尔型产物的对映选择性合成
RSC Adv. 2022 Nov 9;12(49):32056-32060. doi: 10.1039/d2ra06416b. eCollection 2022 Nov 3.
2
Direct β-selectivity of α,β-unsaturated γ-butyrolactam for asymmetric conjugate additions in an organocatalytic manner.α,β-不饱和γ-丁内酰胺以有机催化方式进行不对称共轭加成反应时的直接β-选择性。
RSC Adv. 2018 Aug 14;8(51):28874-28878. doi: 10.1039/c8ra05264f.
3
New Developments of the Principle of Vinylogy as Applied to π-Extended Enolate-Type Donor Systems.
作为应用于π-扩展烯醇型给体体系的 vinylogy 原理的新进展。
Chem Rev. 2020 Mar 11;120(5):2448-2612. doi: 10.1021/acs.chemrev.9b00481. Epub 2020 Feb 10.
4
Effective synthesis of some novel pyrazolidine-3,5-dione derivatives via Mg(II) catalyzed in water medium and their anticancer and antimicrobial activities.通过 Mg(II) 在水相介质中催化合成了一些新型吡唑烷-3,5-二酮衍生物及其抗癌和抗菌活性。
Mol Divers. 2019 Feb;23(1):35-53. doi: 10.1007/s11030-018-9850-3. Epub 2018 Jul 5.
5
Direct Catalytic Asymmetric Doubly Vinylogous Michael Addition of α,β-Unsaturated γ-Butyrolactams to Dienones.α,β-不饱和γ-丁内酰胺与双烯酮的直接催化不对称双烯丙基迈克尔加成反应
Angew Chem Int Ed Engl. 2015 Aug 24;54(35):10249-53. doi: 10.1002/anie.201504276. Epub 2015 Jul 15.
6
Diastereoselective radical addition to γ-alkyl-α-methylene-γ-butyrolactams and the synthesis of a chiral pyroglutamic acid derivative.立体选择性自由基加成到γ-烷基-α-亚甲基-γ-丁内酰胺和手性吡咯烷酮酸衍生物的合成。
Beilstein J Org Chem. 2013 Jul 17;9:1432-6. doi: 10.3762/bjoc.9.161. eCollection 2013.
7
Mild and rapid hydroxylation of aryl/heteroaryl boronic acids and boronate esters with N-oxides.芳基/杂芳基硼酸和硼酸酯的温和快速羟化作用与 N-氧化物。
Org Lett. 2012 Jul 6;14(13):3494-7. doi: 10.1021/ol301463c. Epub 2012 Jun 26.