• 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

对亚氨基丙二酸酯进行双亲核加成反应，从而合成季铵化α-氨基二酯并使产物去对称化。

Double nucleophilic addition to iminomalonate, leading to the synthesis of quaternary α-amino diesters and desymmetrization of the products.

作者信息

Shimizu Makoto, Mushika Miki, Mizota Isao, Zhu Yusong

机构信息

School of Energy Science and Engineering, Nanjing Tech University Nanjing 211816 Jiangsu Province China.

Department of Chemistry for Materials, Graduate School of Engineering, Mie University Tsu Mie 514-8507 Japan

出版信息

RSC Adv. 2019 Jul 29;9(40):23400-23407. doi: 10.1039/c9ra04889h. eCollection 2019 Jul 23.

DOI:10.1039/c9ra04889h
PMID:35514493
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9067299/
Abstract

Alkylation of iminomalonate with Grignard reagents followed by oxidation and allylation gave symmetrical quaternary α-amino diesters in good yields. Subsequent desymmetrization of a diol derivative from these products was conducted asymmetric carbamylation catalyzed by Cu-Bnbox to give chiral quaternary aminodiol mono-carbamates.

摘要

亚氨基丙二酸酯与格氏试剂进行烷基化反应，随后进行氧化和烯丙基化反应，以良好的产率得到对称的季铵化α-氨基二酯。随后，通过Cu-Bnbox催化的不对称氨基甲酰化反应对这些产物中的二醇衍生物进行去对称化，得到手性季铵化氨基二醇单氨基甲酸酯。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1d5/9067299/0f94d033e7d9/c9ra04889h-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1d5/9067299/ced6394247ca/c9ra04889h-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1d5/9067299/4465cd0f27bd/c9ra04889h-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1d5/9067299/92c519801aa6/c9ra04889h-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1d5/9067299/a700d720bee1/c9ra04889h-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1d5/9067299/0f94d033e7d9/c9ra04889h-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1d5/9067299/ced6394247ca/c9ra04889h-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1d5/9067299/4465cd0f27bd/c9ra04889h-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1d5/9067299/92c519801aa6/c9ra04889h-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1d5/9067299/a700d720bee1/c9ra04889h-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1d5/9067299/0f94d033e7d9/c9ra04889h-s4.jpg

相似文献

1
Double nucleophilic addition to iminomalonate, leading to the synthesis of quaternary α-amino diesters and desymmetrization of the products.对亚氨基丙二酸酯进行双亲核加成反应，从而合成季铵化α-氨基二酯并使产物去对称化。
RSC Adv. 2019 Jul 29;9(40):23400-23407. doi: 10.1039/c9ra04889h. eCollection 2019 Jul 23.
2
Enantioselective synthesis of alpha-quaternary amino acid derivatives by sequential enzymatic desymmetrization and Curtius rearrangement of alpha,alpha-disubstituted malonate diesters.通过连续的酶不对称解和α,α-二取代丙二酸二酯的Curtius 重排反应对α-季铵氨基酸衍生物的对映选择性合成。
J Org Chem. 2010 Mar 5;75(5):1612-9. doi: 10.1021/jo902584r.
3
Stereodivergent Desymmetrization of Simple Dicarboxylates via Branch-Selective Pd/Cu Catalyzed Allylic Substitution.通过支链选择性钯/铜催化的烯丙基取代实现简单二羧酸酯的立体发散性去对称化
Chemistry. 2022 Apr 27;28(24):e202200273. doi: 10.1002/chem.202200273. Epub 2022 Mar 24.
4
Desymmetrization of Inert -Diethers through Copper-Catalyzed Asymmetric Allylic Alkylation with Grignard Reagents.通过铜催化的格氏试剂不对称烯丙基烷基化实现惰性二醚的去对称化
Org Lett. 2024 Jul 12;26(27):5844-5849. doi: 10.1021/acs.orglett.4c01972. Epub 2024 Jul 1.
5
Silver-Catalyzed Asymmetric Double Desymmetrization via Vinylogous Michael Addition of Prochiral α,α-Dicyanoalkenes to Cyclopentendiones.通过前手性α,α-二氰基烯烃与环戊二酮的烯丙基迈克尔加成实现银催化的不对称双去对称化反应
Chemistry. 2024 Apr 5;30(20):e202304078. doi: 10.1002/chem.202304078. Epub 2024 Feb 20.
6
Asymmetric Synthesis of a Quaternary Carbon Stereogenic Center by Organocatalysis Using a Primary Amino Acid and Its Salt.使用伯氨基酸及其盐通过有机催化实现季碳立体中心的不对称合成。
Chem Rec. 2023 Jul;23(7):e202200276. doi: 10.1002/tcr.202200276. Epub 2023 Feb 2.
7
Chiral Aldehyde Catalysis-Enabled Asymmetric α-Functionalization of Activated Primary Amines.手性醛催化实现的活化伯胺的不对称α-官能团化
Acc Chem Res. 2024 Mar 5;57(5):776-794. doi: 10.1021/acs.accounts.3c00804. Epub 2024 Feb 21.
8
Chromium(III)-Catalyzed Desymmetrization of -Epoxides via Remote Stereocontrol: Synthesis of Chiral Fluorenes Bearing All-Carbon Quaternary Stereocenters.铬（III）催化的环氧化合物远程立体控制去对称化反应：含全碳季碳立体中心的手性芴的合成。
Org Lett. 2024 Feb 2;26(4):877-882. doi: 10.1021/acs.orglett.3c04144. Epub 2024 Jan 24.
9
Chiral diphosphine and monodentate phosphorus ligands on a spiro scaffold for transition-metal-catalyzed asymmetric reactions.用于过渡金属催化不对称反应的螺环骨架上的手性双膦和单齿磷配体
Acc Chem Res. 2008 May;41(5):581-93. doi: 10.1021/ar700137z. Epub 2008 Mar 1.
10
Access to N-α-quaternary chiral morpholines via Cu-catalyzed asymmetric propargylic amination/desymmetrization strategy.通过铜催化的不对称炔丙基胺化/去对称化策略获得N-α-季碳手性吗啉。
Sci Bull (Beijing). 2024 Nov 30;69(22):3516-3524. doi: 10.1016/j.scib.2024.08.005. Epub 2024 Aug 8.

引用本文的文献

1
Preparation and facile addition reactions of iminium salts derived from amino ketene silyl acetal and amino silyl enol ether.由氨基烯酮硅基缩醛和氨基硅基烯醇醚衍生的亚胺盐的制备及其简便的加成反应
RSC Adv. 2020 Jul 24;10(46):27874-27883. doi: 10.1039/d0ra05768a. eCollection 2020 Jul 21.
2
An umpolung reaction of α-iminothioesters possessing a cyclopropyl group.具有环丙基的α-亚氨基硫酯的极性反转反应。
RSC Adv. 2020 Mar 10;10(17):9955-9963. doi: 10.1039/d0ra01152e. eCollection 2020 Mar 6.
3
-Alkylation/aldol reaction of α-aldimino thioesters: a facile three-component coupling reaction.

本文引用的文献

1
A facile approach to 2-alkoxyindolin-3-one and its application to the synthesis of -benzyl matemone.一种合成2-烷氧基吲哚-3-酮的简便方法及其在合成苄基马替莫酮中的应用。
RSC Adv. 2019 Jun 3;9(30):17341-17346. doi: 10.1039/c9ra02204j. eCollection 2019 May 29.
2
Tandem N, N-Dialkylation Reaction of N-Trimethylsilyl α-Iminoesters Utilizing an Umpolung Reaction and Characteristics of the Silyl Substituent: Synthesis of Pyrrolidine, Piperidine, and Iminodiacetate.利用极性翻转反应的N-三甲基硅基α-亚氨基酯的串联N，N-二烷基化反应及硅基取代基的特性：吡咯烷、哌啶和亚氨基二乙酸酯的合成
Org Lett. 2019 Apr 19;21(8):2663-2667. doi: 10.1021/acs.orglett.9b00654. Epub 2019 Apr 8.
3
-α-醛亚胺硫酯的烷基化/羟醛反应：一种简便的三组分偶联反应。
RSC Adv. 2021 Apr 7;11(22):13097-13104. doi: 10.1039/d1ra02000e.
Organoselenium-Based Entry into Versatile, α-(2-Tributylstannyl)vinyl Amino Acids in Scalemic Form: A New Route to Vinyl Stannanes.
基于有机硒的手性α-(2-三丁基锡基)乙烯基氨基酸的合成：乙烯基锡烷的新合成路线。
J Am Chem Soc. 2000 Nov 8;122(44):11031-11032. doi: 10.1021/ja0055110. Epub 2000 Oct 21.
4
Umpolung Reactions of α-Imino Esters: Useful Methods for the Preparation of α-Amino Acid Frameworks.α-亚氨基酯的极性反转反应：制备α-氨基酸骨架的有用方法。
Chem Rec. 2016 Apr;16(2):688-702. doi: 10.1002/tcr.201500267. Epub 2016 Feb 2.
5
Recent Advances in Lipase-Mediated Preparation of Pharmaceuticals and Their Intermediates.脂肪酶介导的药物及其中间体制备的最新进展
Int J Mol Sci. 2015 Dec 11;16(12):29682-716. doi: 10.3390/ijms161226191.
6
Recent Advances in Asymmetric Catalytic Methods for the Formation of Acyclic α,α-Disubstituted α-Amino Acids.用于形成无环α,α-二取代α-氨基酸的不对称催化方法的最新进展
J Org Chem. 2015 Jan 2;80(1):1-7. doi: 10.1021/jo502408z. Epub 2014 Dec 11.
7
Asymmetric synthesis of α-allyl-α-aryl α-amino acids by tandem alkylation/π-allylation of α-iminoesters.通过α-亚氨基酯的串联烷基化/π-烯丙基化反应实现α-烯丙基-α-芳基-α-氨基酸的不对称合成。
Org Lett. 2014 Apr 4;16(7):1948-51. doi: 10.1021/ol500506t. Epub 2014 Mar 25.
8
Asymmetric α-arylation of amino acid derivatives by Clayden rearrangement of ester enolates via memory of chirality.手性通过酯烯醇化物克莱森重排的氨基酸衍生物的不对称 α-芳基化。
J Am Chem Soc. 2013 Sep 11;135(36):13294-7. doi: 10.1021/ja406653n. Epub 2013 Aug 27.
9
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.
10
Enantioselective synthesis of alpha-quaternary amino acid derivatives by sequential enzymatic desymmetrization and Curtius rearrangement of alpha,alpha-disubstituted malonate diesters.通过连续的酶不对称解和α,α-二取代丙二酸二酯的Curtius 重排反应对α-季铵氨基酸衍生物的对映选择性合成。
J Org Chem. 2010 Mar 5;75(5):1612-9. doi: 10.1021/jo902584r.