• 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

基于L-氨基酸的脲-叔胺催化3-溴氧化吲哚与丙二酸半硫酯的化学选择性和不对称立体消融羧基化反应

L-Amino Acid Based Urea-Tertiary Amine-Catalyzed Chemoselective and Asymmetric Stereoablative Carboxylation of 3-Bromooxindoles with Malonic Acid Half Thioesters.

作者信息

Bai Xiangbin, Jing Zhenzhong, Liu Qian, Ye Xinyi, Zhang Gao, Zhao Xiaowei, Jiang Zhiyong

机构信息

Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University , Kaifeng, Henan, P. R. China , 475004.

Division of Chemistry and Biological Chemistry, Nanyang Technological University , 21 Nanyang Link, 637371, Singapore.

出版信息

J Org Chem. 2015 Dec 18;80(24):12686-96. doi: 10.1021/acs.joc.5b02286. Epub 2015 Nov 12.

DOI:10.1021/acs.joc.5b02286
PMID:26544639
Abstract

An L-amino acid based urea-tertiary amine-catalyzed enantioselective stereoablative carboxylation of 3-bromooxindoles with malonic acid half thioesters (MAHTs) and diverse commercially available carboxylic acids has been developed. A series of valuable 3-substituted 3-hydroxy-2-oxindoles were obtained in high enantioselectivities (up to 93% ee). This chemoselective reaction represents the first example of MAHTs as carboxylating agents.

摘要

基于L-氨基酸的脲-叔胺催化3-溴氧化吲哚与丙二酸半硫酯(MAHTs)及多种市售羧酸的对映选择性立体消旋羧化反应已被开发出来。一系列有价值的3-取代-3-羟基-2-氧化吲哚以高对映选择性(高达93% ee)得到。这种化学选择性反应代表了MAHTs作为羧化剂的首例。

相似文献

1
L-Amino Acid Based Urea-Tertiary Amine-Catalyzed Chemoselective and Asymmetric Stereoablative Carboxylation of 3-Bromooxindoles with Malonic Acid Half Thioesters.基于L-氨基酸的脲-叔胺催化3-溴氧化吲哚与丙二酸半硫酯的化学选择性和不对称立体消融羧基化反应
J Org Chem. 2015 Dec 18;80(24):12686-96. doi: 10.1021/acs.joc.5b02286. Epub 2015 Nov 12.
2
Asymmetric decarboxylative 1,4-addition of malonic acid half thioesters to vinyl sulfones: highly enantioselective synthesis of 3-monofluoromethyl-3-arylpropanoic esters.丙二酸半硫酯与乙烯基砜的不对称脱羧1,4-加成反应:3-单氟甲基-3-芳基丙酸酯的高对映选择性合成
Chem Asian J. 2014 May;9(5):1252-6. doi: 10.1002/asia.201400049. Epub 2014 Mar 3.
3
Asymmetric Michael addition reaction of 3-substituted-N-Boc oxindoles to activated terminal alkenes catalyzed by a bifunctional tertiary-amine thiourea catalyst.双功能叔胺硫脲催化 3-取代-N-Boc 氧吲哚与活化末端烯烃的不对称迈克尔加成反应。
Org Biomol Chem. 2010 Jan 7;8(1):77-82. doi: 10.1039/b918644a. Epub 2009 Oct 29.
4
Gaining Insight Into Reactivity Differences Between Malonic Acid Half Thioesters (MAHT) and Malonic Acid Half Oxyesters (MAHO).深入了解丙二酸半硫酯(MAHT)和丙二酸半氧酯(MAHO)之间的反应活性差异。
Chemistry. 2017 Apr 3;23(19):4557-4569. doi: 10.1002/chem.201605148. Epub 2017 Jan 31.
5
Organocatalytic enantioselective decarboxylative reaction of malonic acid half thioesters with cyclic N-sulfonyl ketimines by using N-heteroarenesulfonyl cinchona alkaloid amides.通过使用氮杂芳基磺酰基金鸡纳生物碱酰胺实现丙二酸半硫酯与环状N-磺酰基酮亚胺的有机催化对映选择性脱羧反应。
Chemistry. 2015 Mar 2;21(10):3929-32. doi: 10.1002/chem.201406270. Epub 2015 Jan 22.
6
Chiral Bicyclic Guanidine-Catalyzed Enantioselective Sulfenylation of Oxindoles and Benzofuran-2(3H)-ones.手性双环胍催化的氧化吲哚和苯并呋喃-2(3H)-酮的对映选择性亚磺酰化反应
J Org Chem. 2015 Sep 4;80(17):8933-41. doi: 10.1021/acs.joc.5b01606. Epub 2015 Aug 12.
7
Decarboxylative Organocatalyzed Addition Reactions of Fluoroacetate Surrogates for the Synthesis of Fluorinated Oxindoles.脱羧有机催化氟乙酸酯类似物的加成反应在氟代色酮合成中的应用。
Org Lett. 2021 Mar 5;23(5):1753-1757. doi: 10.1021/acs.orglett.1c00172. Epub 2021 Feb 16.
8
An exceptionally mild catalytic thioester aldol reaction inspired by polyketide biosynthesis.受聚酮生物合成启发的一种极其温和的催化硫酯醛醇缩合反应。
J Am Chem Soc. 2003 Mar 12;125(10):2852-3. doi: 10.1021/ja029452x.
9
Malonic acid half oxyesters and thioesters: solvent-free synthesis and DFT analysis of their enols.丙二酸半酯和硫代酯:无溶剂合成及其烯醇的密度泛函理论分析。
Org Lett. 2013 Aug 2;15(15):3805-7. doi: 10.1021/ol400804b. Epub 2013 Jul 22.
10
Enantioselective Morita-Baylis-Hillman reaction of isatins with acrylates: facile creation of 3-hydroxy-2-oxindoles.手性诱导的异吲哚啉酮与丙烯酸酯的 Morita-Baylis-Hillman 反应:3-羟基-2-氧代吲哚的简便构建。
Org Lett. 2011 Jan 7;13(1):82-5. doi: 10.1021/ol102597s. Epub 2010 Dec 3.

引用本文的文献

1
α-Halocarbonyls as a Valuable Functionalized Tertiary Alkyl Source.α-卤代羰基化合物作为一种重要的官能化叔烷基来源。
ChemistryOpen. 2024 Oct;13(10):e202400108. doi: 10.1002/open.202400108. Epub 2024 Jul 11.
2
Chiral acid-catalysed enantioselective C-H functionalization of toluene and its derivatives driven by visible light.可见光驱动的手性酸催化甲苯及其衍生物的对映选择性C-H官能团化反应
Nat Commun. 2019 Apr 16;10(1):1774. doi: 10.1038/s41467-019-09857-9.
3
Alcohols as Substrates and Solvents for the Construction of 3-Alkoxylated-2-Oxindoles by Direct Alkoxylation of 3-Halooxindoles.
通过3-卤代氧化吲哚的直接烷氧基化反应,以醇类作为底物和溶剂构建3-烷氧基化-2-氧化吲哚
Molecules. 2017 May 13;22(5):801. doi: 10.3390/molecules22050801.