• 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

非环烯丙基醚与有机锂试剂的不对称烯丙基烷基化反应。

Asymmetric allylic alkylation of acyclic allylic ethers with organolithium reagents.

机构信息

Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands.

出版信息

Chemistry. 2012 Sep 17;18(38):11880-3. doi: 10.1002/chem.201202251. Epub 2012 Aug 21.

DOI:10.1002/chem.201202251
PMID:22907628
Abstract

A highly efficient, regio- and enantioselective Cu(I)/phosphoramidite-catalyzed asymmetric allylic alkylation of allyl ethers with organolithium reagents is reported (see scheme). The use of organolithium reagents is essential for this catalytic C-C bond formation due to their compatibility with different Lewis acids. The versatility of allylic ethers under the copper-catalyzed reaction conditions with organolithium reagents is demonstrated in the shortest synthesis of (S)-Arundic acid.

摘要

本文报道了一种高效、区域和对映选择性的铜(I)/磷酰胺催化剂促进的烯丙基醚与有机锂试剂的不对称烯丙基烷基化反应(见方案)。由于其与不同路易斯酸的兼容性,有机锂试剂对于这种催化 C-C 键形成是必不可少的。在铜催化的与有机锂试剂的反应条件下,烯丙基醚的多功能性在(S)-芦竹碱的最短合成中得到了证明。

相似文献

1
Asymmetric allylic alkylation of acyclic allylic ethers with organolithium reagents.非环烯丙基醚与有机锂试剂的不对称烯丙基烷基化反应。
Chemistry. 2012 Sep 17;18(38):11880-3. doi: 10.1002/chem.201202251. Epub 2012 Aug 21.
2
Cu-catalyzed enantioselective allylic alkylation with organolithium reagents.铜催化的手性烯丙基烷基化与有机锂试剂。
Nat Protoc. 2017 Mar;12(3):493-505. doi: 10.1038/nprot.2016.179. Epub 2017 Feb 2.
3
Chiral Diarylmethanes via Copper-Catalyzed Asymmetric Allylic Arylation with Organolithium Compounds.手性二芳基甲烷的铜催化不对称烯丙基芳基化与有机锂化合物。
Org Lett. 2016 Jan 15;18(2):252-5. doi: 10.1021/acs.orglett.5b03396. Epub 2015 Dec 23.
4
Z-Selective copper-catalyzed asymmetric allylic alkylation with Grignard reagents.Z-选择性铜催化的不对称烯丙基烷基化与格氏试剂。
J Am Chem Soc. 2012 Mar 7;134(9):4108-11. doi: 10.1021/ja300743t. Epub 2012 Feb 27.
5
Synthesis of optically active β- or γ-alkyl-substituted alcohols through copper-catalyzed asymmetric allylic alkylation with organolithium reagents.通过铜催化的不对称烯丙基烷基化反应与有机锂试剂反应,合成手性β-或γ-烷基取代的醇。
J Org Chem. 2013 Sep 6;78(17):8274-80. doi: 10.1021/jo401536u. Epub 2013 Aug 23.
6
Catalytic enantioselective synthesis of quaternary all-carbon stereogenic centers. Preparation of alpha,alpha'-disubstituted beta,gamma-unsaturated esters through Cu-catalyzed asymmetric allylic alkylations.季碳全碳立体中心的催化对映选择性合成。通过铜催化的不对称烯丙基烷基化反应制备α,α'-二取代的β,γ-不饱和酯。
Org Lett. 2005 Mar 31;7(7):1255-8. doi: 10.1021/ol047331r.
7
Hydrogen-bond-activated palladium-catalyzed allylic alkylation via allylic alkyl ethers: challenging leaving groups.氢键活化钯催化的烯丙基烷基化反应通过烯丙基烷基醚:具有挑战性的离去基团。
Org Lett. 2014 Mar 21;16(6):1570-3. doi: 10.1021/ol5000988. Epub 2014 Mar 12.
8
Enantioselective synthesis of all-carbon quaternary stereogenic centers via copper-catalyzed asymmetric allylic alkylation of (Z)-allyl bromides with organolithium reagents.通过铜催化(Z)-烯丙基溴与有机锂试剂的不对称烯丙基烷基化反应对全碳季碳手性中心进行对映选择性合成。
Chemistry. 2015 Mar 9;21(11):4209-12. doi: 10.1002/chem.201406006. Epub 2015 Jan 28.
9
Omega-ethylenic allylic substrates as alternatives to cyclic substrates in copper- and iridium-catalyzed asymmetric allylic alkylation.在铜和铱催化的不对称烯丙基烷基化反应中,作为环状底物的替代物,使用ω-乙基烯丙基亲电试剂。
Org Lett. 2010 Mar 19;12(6):1156-9. doi: 10.1021/ol100162y.
10
Highly site- and enantioselective Cu-catalyzed allylic alkylation reactions with easily accessible vinylaluminum reagents.使用易于获得的乙烯基铝试剂进行的高度位点和对映选择性铜催化的烯丙基烷基化反应。
J Am Chem Soc. 2008 Jan 16;130(2):446-7. doi: 10.1021/ja0782192. Epub 2007 Dec 19.

引用本文的文献

1
Copper-catalyzed asymmetric allylic alkylation of racemic inert cyclic allylic ethers under batch and flow conditions.外消旋惰性环状烯丙基醚在间歇和连续流动条件下的铜催化不对称烯丙基烷基化反应
Chem Sci. 2023 Mar 22;14(16):4351-4356. doi: 10.1039/d3sc00127j. eCollection 2023 Apr 26.
2
Transition-metal-free allylation of 2-azaallyls with allyl ethers through polar and radical mechanisms.通过极性和自由基机制实现2-氮杂烯丙基与烯丙基醚的无过渡金属烯丙基化反应。
Nat Commun. 2021 Jun 23;12(1):3860. doi: 10.1038/s41467-021-24027-6.
3
Cross-Coupling Reaction of Allylic Ethers with Aryl Grignard Reagents Catalyzed by a Nickel Pincer Complex.
烯丙基醚与芳基格氏试剂的交叉偶联反应在镍钳形配合物催化下进行。
Molecules. 2019 Jun 21;24(12):2296. doi: 10.3390/molecules24122296.
4
Desymmetrization of meso-Dibromocycloalkenes through Copper(I)-Catalyzed Asymmetric Allylic Substitution with Organolithium Reagents.通过铜(I)催化的不对称烯丙基取代反应,用有机锂试剂对介-Dibromocycloalkenes 进行去对称化。
J Am Chem Soc. 2018 Jun 13;140(23):7052-7055. doi: 10.1021/jacs.8b02992. Epub 2018 May 31.
5
Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.用于构建碳-碳键的有机金属试剂的对映选择性和对映特异性过渡金属催化交叉偶联反应。
Chem Rev. 2015 Sep 9;115(17):9587-652. doi: 10.1021/acs.chemrev.5b00162. Epub 2015 Aug 13.