• 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

手性噁唑烷二酮衍生物作为氢键催化剂用于 1,3-二羰基化合物的对映选择性α-氨基化反应。

Enantioselective alpha-amination of 1,3-dicarbonyl compounds using squaramide derivatives as hydrogen bonding catalysts.

机构信息

Department of Chemistry, University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, USA.

出版信息

Org Lett. 2010 May 7;12(9):2028-31. doi: 10.1021/ol1005104.

DOI:10.1021/ol1005104
PMID:20359172
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2862278/
Abstract

Catalytic enantioselective alpha-hydrazination of 1,3-dicarbonyl compounds with azodicarboxylates was investigated in the presence of our newly developed hydrogen bonding catalyst, squaramide 3j. High yields and high enantioselectivities were achieved with low catalyst loading under mild conditions.

摘要

在我们新开发的氢键催化剂——螺二酰胺 3j 的存在下，研究了 1,3-二羰基化合物与重氮二甲酸酯的催化对映选择性α-酰腙化反应。在温和条件下，只需低催化剂负载量即可获得高产率和高对映选择性。

相似文献

1
Enantioselective alpha-amination of 1,3-dicarbonyl compounds using squaramide derivatives as hydrogen bonding catalysts.手性噁唑烷二酮衍生物作为氢键催化剂用于 1,3-二羰基化合物的对映选择性α-氨基化反应。
Org Lett. 2010 May 7;12(9):2028-31. doi: 10.1021/ol1005104.
2
Cinchona alkaloid squaramide catalyzed enantioselective hydrazination/cyclization cascade reaction of α-isocyanoacetates and azodicarboxylates: synthesis of optically active 1,2,4-triazolines.金鸡纳生物碱螺缩酰胺催化的 α-异氰基乙酸酯和偶氮二甲酸酯的对映选择性酰肼化/环化串联反应：光学活性 1,2,4-三唑啉的合成。
J Org Chem. 2013 Sep 20;78(18):9377-82. doi: 10.1021/jo401585v. Epub 2013 Aug 28.
3
Chiral squaramide derivatives are excellent hydrogen bond donor catalysts.手性方酰胺衍生物是优异的氢键供体催化剂。
J Am Chem Soc. 2008 Nov 5;130(44):14416-7. doi: 10.1021/ja805693p. Epub 2008 Oct 11.
4
Highly enantioselective synthesis of 3-amino-2-oxindole derivatives: catalytic asymmetric alpha-amination of 3-substituted 2-oxindoles with a chiral scandium complex.高对映选择性合成 3-氨基-2-氧吲哚衍生物：手性钪配合物催化 3-取代 2-氧吲哚的不对称α-胺化反应。
Chemistry. 2010 Jun 11;16(22):6632-7. doi: 10.1002/chem.201000126.
5
Enantioselective amination of nitroolefins under base-free and water-rich conditions using chiral bifunctional phase-transfer catalysts.手性双功能相转移催化剂在无碱和富水条件下对硝基烯烃的对映选择性胺化反应。
Org Biomol Chem. 2018 Apr 25;16(16):3012-3017. doi: 10.1039/c8ob00583d.
6
Enantioselective synthesis of coumarins catalyzed by an isosteviol-derived tertiary amine-squaramide catalyst.由异甜菊醇衍生的叔胺-双缩胍催化剂催化的香豆素的对映选择性合成。
Chirality. 2022 Feb;34(2):325-332. doi: 10.1002/chir.23401. Epub 2021 Dec 13.
7
Asymmetric construction of quaternary stereocenters by direct organocatalytic amination of alpha-substituted alpha-cyanoacetates and beta-dicarbonyl compounds.通过α-取代的α-氰基乙酸酯与β-二羰基化合物的直接有机催化胺化反应构建季碳立体中心的不对称合成。
J Am Chem Soc. 2004 Jul 7;126(26):8120-1. doi: 10.1021/ja047704j.
8
Readily Available Chiral Benzimidazoles-Derived Guanidines as Organocatalysts in the Asymmetric α-Amination of 1,3-Dicarbonyl Compounds.易于获得的手性苯并咪唑衍生胍作为1,3-二羰基化合物不对称α-胺化反应中的有机催化剂
Molecules. 2017 Aug 11;22(8):1333. doi: 10.3390/molecules22081333.
9
Bifunctional hydrogen-bond donors that bear a quinazoline or benzothiadiazine skeleton for asymmetric organocatalysis.具有喹唑啉或苯并噻二嗪骨架的双功能氢键供体，用于不对称有机催化。
Chemistry. 2011 Sep 5;17(37):10470-7. doi: 10.1002/chem.201101338. Epub 2011 Aug 2.
10
Enantioselective Amination of β-Keto Esters Catalyzed by Chiral Calcium Phosphates.手性钙磷酸盐催化的β-酮酯的对映选择性胺化反应。
Chemistry. 2022 Jul 1;28(37):e202200907. doi: 10.1002/chem.202200907. Epub 2022 May 23.

引用本文的文献

1
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.
2
Mechanochemical Thiolation of α-Imino Ketones: A Catalyst-Free, One-Pot, Three-Component Reaction.α-亚氨基酮的机械化学硫醇化反应：一种无催化剂的一锅三组分反应
ACS Omega. 2025 Jan 29;10(5):4636-4650. doi: 10.1021/acsomega.4c09218. eCollection 2025 Feb 11.
3
Antibacterial Activity of Squaric Amide Derivative SA2 against Methicillin-Resistant .方酸酰胺衍生物SA2对耐甲氧西林菌的抗菌活性
Antibiotics (Basel). 2022 Oct 28;11(11):1497. doi: 10.3390/antibiotics11111497.
4
Efficiency and Suitability when Exploring the Conformational Space of Phase-Transfer Catalysts.当探索相转移催化剂的构象空间时的效率和适宜性。
J Chem Inf Model. 2022 Nov 28;62(22):5568-5580. doi: 10.1021/acs.jcim.2c00934. Epub 2022 Oct 22.
5
Enantioselective amination of 4-alkylisoquinoline-1,3(2,4)-dione derivatives.4-烷基异喹啉-1,3(2,4)-二酮衍生物的对映选择性胺化反应
RSC Adv. 2020 Nov 25;10(70):42912-42915. doi: 10.1039/d0ra07806a. eCollection 2020 Nov 23.
6
Metal-free multicomponent approach for the synthesis of propargylamine: a review.用于合成炔丙胺的无金属多组分方法：综述
RSC Adv. 2021 Jan 7;11(4):2047-2065. doi: 10.1039/d0ra09392k. eCollection 2021 Jan 6.
7
Bifunctional Iminophosphorane-Catalyzed Enantioselective Sulfa-Michael Addition to Unactivated α,β-Unsaturated Amides.双功能亚膦酰胺催化的对未活化的α,β-不饱和酰胺的对映选择性亚砜迈克尔加成反应。
J Am Chem Soc. 2022 Jan 19;144(2):1006-1015. doi: 10.1021/jacs.1c11898. Epub 2022 Jan 6.
8
A bifunctional iminophosphorane squaramide catalyzed enantioselective synthesis of hydroquinazolines intramolecular aza-Michael reaction to α,β-unsaturated esters.一种双功能亚胺基磷烷方酰胺催化对映选择性合成氢喹唑啉的分子内氮杂-Michael反应与α,β-不饱和酯。
Chem Sci. 2021 Mar 18;12(17):6064-6072. doi: 10.1039/d1sc00856k.
9
Cinchona Squaramide-Based Chiral Polymers as Highly Efficient Catalysts in Asymmetric Michael Addition Reaction.基于金鸡纳方酰胺的手性聚合物在不对称迈克尔加成反应中作为高效催化剂
ACS Omega. 2018 Apr 26;3(4):4573-4582. doi: 10.1021/acsomega.8b00398. eCollection 2018 Apr 30.
10
Mannich-type Reactions of Cyclic Nitrones: Effective Methods for the Enantioselective Synthesis of Piperidine-containing Alkaloids.曼尼希型反应的环状亚硝酮：含哌啶生物碱的对映选择性合成的有效方法。
Angew Chem Int Ed Engl. 2018 Nov 12;57(46):15162-15166. doi: 10.1002/anie.201809799. Epub 2018 Oct 19.

本文引用的文献

1
Catalytic Enantioselective Electrophilic Aminations of Acyclic α-Alkyl β-Carbonyl Nucleophilies.无环α-烷基β-羰基亲核试剂的催化对映选择性亲电胺化反应
Synlett. 2009 Jun;10:1685-1689. doi: 10.1055/s-0029-1217334.
2
Recent Progress on the Stereoselective Synthesis of Cyclic Quaternary alpha-Amino Acids.环状季铵α-氨基酸立体选择性合成的最新进展
Tetrahedron Asymmetry. 2009 Jan 30;20(1):1-63. doi: 10.1016/j.tetasy.2009.01.002.
3
Squaramide-catalyzed enantioselective Michael addition of diphenyl phosphite to nitroalkenes.席夫碱催化的膦酸二苯酯对硝基烯烃的对映选择性迈克尔加成反应。
Angew Chem Int Ed Engl. 2010;49(1):153-6. doi: 10.1002/anie.200904779.
4
Self-association-free dimeric cinchona alkaloid organocatalysts: unprecedented catalytic activity, enantioselectivity and catalyst recyclability in dynamic kinetic resolution of racemic azlactones.无自缔合二聚体奎宁生物碱有机催化剂：在消旋氮杂环丁酮的动态动力学拆分中具有前所未有的催化活性、对映选择性和催化剂可回收性。
Chem Commun (Camb). 2009 Dec 14(46):7224-6. doi: 10.1039/b917882a. Epub 2009 Oct 16.
5
Managing highly coordinative substrates in asymmetric catalysis: a catalytic asymmetric amination with a lanthanum-based ternary catalyst.在手性催化中管理高协同底物：一种基于镧的三元催化剂的催化不对称胺化反应。
J Am Chem Soc. 2009 Oct 21;131(41):14990-9. doi: 10.1021/ja9052653.
6
Diastereoselective and enantioselective synthesis of tertiary alpha-hydroxy phosphonates through hydrogen-bond catalysis.通过氢键催化实现叔α-羟基膦酸酯的非对映选择性和对映选择性合成。
Angew Chem Int Ed Engl. 2009;48(4):776-9. doi: 10.1002/anie.200804244.
7
Binaphthyl-modified quaternary phosphonium salts as chiral phase-transfer catalysts: asymmetric amination of beta-keto esters.联萘修饰的季鏻盐作为手性相转移催化剂：β-酮酯的不对称胺化反应
Angew Chem Int Ed Engl. 2008;47(49):9466-8. doi: 10.1002/anie.200804140.
8
Chiral squaramide derivatives are excellent hydrogen bond donor catalysts.手性方酰胺衍生物是优异的氢键供体催化剂。
J Am Chem Soc. 2008 Nov 5;130(44):14416-7. doi: 10.1021/ja805693p. Epub 2008 Oct 11.
9
An improved lanthanum catalyst system for asymmetric amination: toward a practical asymmetric synthesis of AS-3201 (Ranirestat).一种用于不对称胺化的改进镧催化剂体系：迈向AS-3201（雷尼司他）的实用不对称合成。
Org Lett. 2008 Jul 3;10(13):2725-8. doi: 10.1021/ol8008446. Epub 2008 Jun 4.
10
Carbon-nitrogen bond-forming reactions of dialkyl azodicarboxylate: a promising synthetic strategy.偶氮二甲酸二烷基酯的碳-氮键形成反应：一种有前景的合成策略。
Chem Asian J. 2008 May 5;3(5):810-20. doi: 10.1002/asia.200700341.