• 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

镍催化的炔烃与醛的对映选择性烷基化偶联反应:合成具有四取代烯烃的手性烯丙醇

Nickel-catalyzed enantioselective alkylative coupling of alkynes and aldehydes: synthesis of chiral allylic alcohols with tetrasubstituted olefins.

作者信息

Yang Yun, Zhu Shou-Fei, Zhou Chang-Yue, Zhou Qi-Lin

机构信息

State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China.

出版信息

J Am Chem Soc. 2008 Oct 29;130(43):14052-3. doi: 10.1021/ja805296k. Epub 2008 Oct 4.

DOI:10.1021/ja805296k
PMID:18834121
Abstract

A highly efficient nickel-catalyzed asymmetric alkylative coupling of alkynes, aldehydes, and dimethylzinc has been realized by using bulky spirobiindane phosphoramidite ligands, affording allylic alcohols with a tetrasubstituted olefin functionality in high yields, high regioselectivities, and excellent enantioselectivities.

摘要

通过使用庞大的螺双茚满亚磷酰胺配体,实现了镍催化的炔烃、醛和二甲基锌的高效不对称烷基化偶联反应,以高收率、高区域选择性和优异的对映选择性得到具有四取代烯烃官能团的烯丙醇。

相似文献

1
Nickel-catalyzed enantioselective alkylative coupling of alkynes and aldehydes: synthesis of chiral allylic alcohols with tetrasubstituted olefins.镍催化的炔烃与醛的对映选择性烷基化偶联反应:合成具有四取代烯烃的手性烯丙醇
J Am Chem Soc. 2008 Oct 29;130(43):14052-3. doi: 10.1021/ja805296k. Epub 2008 Oct 4.
2
Nickel-catalyzed enantioselective three-component coupling of bis-1,3-dienes, aldehydes, and dimethylzinc.镍催化的双-1,3-二烯、醛和二甲基锌的对映选择性三组分偶联反应
J Org Chem. 2005 Oct 14;70(21):8605-8. doi: 10.1021/jo051283m.
3
Simple alkenes as substitutes for organometallic reagents: nickel-catalyzed, intermolecular coupling of aldehydes, silyl triflates, and alpha olefins.简单烯烃作为有机金属试剂的替代物:镍催化的醛、三氟甲磺酸硅酯和α-烯烃的分子间偶联反应
J Am Chem Soc. 2005 Oct 19;127(41):14194-5. doi: 10.1021/ja055363j.
4
Access to macrocyclic endocyclic and exocyclic allylic alcohols by nickel-catalyzed reductive cyclization of ynals.通过镍催化的烯醛还原环化反应合成大环内烯丙醇和外烯丙醇
J Am Chem Soc. 2005 Sep 28;127(38):13156-7. doi: 10.1021/ja054590i.
5
Tandem addition/cyclization reaction of organozinc reagents to 2-alkynyl aldehydes: highly efficient regio- and enantioselective synthesis of 1,3-dihydroisobenzofurans and tetrasubstituted furans.有机锌试剂与2-炔基醛的串联加成/环化反应:1,3-二氢异苯并呋喃和四取代呋喃的高效区域和对映选择性合成
J Org Chem. 2008 Apr 4;73(7):2947-50. doi: 10.1021/jo800029m. Epub 2008 Mar 4.
6
Highly enantioselective zinc/amino alcohol-catalyzed alkynylation of aldehydes.高度对映选择性的锌/氨基醇催化的醛的炔基化反应。
Chemistry. 2009;15(13):3069-71. doi: 10.1002/chem.200900070.
7
Rhodium-catalyzed asymmetric tandem cyclization for efficient and rapid access to underexplored heterocyclic tertiary allylic alcohols containing a tetrasubstituted olefin.铑催化的不对称串联环化反应用于高效、快速地获得含有四取代烯烃的未充分探索的杂环叔烯丙醇。
Org Lett. 2014 May 16;16(10):2712-5. doi: 10.1021/ol500993h. Epub 2014 Apr 28.
8
Nickel-catalyzed regioselective synthesis of tetrasubstituted alkene using alkylative carboxylation of disubstituted alkyne.镍催化二取代炔烃的烷基羧化反应区域选择性合成四取代烯烃
Org Lett. 2005 Jan 20;7(2):195-7. doi: 10.1021/ol047912g.
9
Nickel-catalyzed asymmetric negishi cross-couplings of secondary allylic chlorides with alkylzincs.镍催化仲烯丙基氯与烷基锌的不对称根岸交叉偶联反应。
J Am Chem Soc. 2008 Mar 5;130(9):2756-7. doi: 10.1021/ja800103z. Epub 2008 Feb 8.
10
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.

引用本文的文献

1
Cobalt-catalyzed diastereo- and enantioselective reductive coupling of cyclobutenes and aldehydes through umpolung reactivity.钴催化环丁烯与醛通过极性反转反应进行非对映和对映选择性还原偶联。
Chem Sci. 2025 Aug 4. doi: 10.1039/d5sc03755g.
2
Enantioselective electroreductive alkyne-aldehyde coupling.对映选择性电还原炔烃-醛偶联反应
Nat Commun. 2025 Jul 1;16(1):5686. doi: 10.1038/s41467-025-60230-5.
3
Catalytic stereoselective synthesis of all-carbon tetra-substituted alkenes -selective alkyne difunctionalization.全碳四取代烯烃的催化立体选择性合成——选择性炔烃双官能化反应
Chem Sci. 2025 Mar 13;16(15):6273-6281. doi: 10.1039/d5sc00297d. eCollection 2025 Apr 9.
4
Palladium(0)-Catalyzed Anti-Selective Addition-Cyclizations of Alkynyl Electrophiles.钯(0)催化的炔基亲电试剂反选择性加成-环化反应。
Chemistry. 2023 Jan 27;29(6):e202203068. doi: 10.1002/chem.202203068. Epub 2022 Dec 20.
5
Rapid access to -butylalkylated olefins enabled by Ni-catalyzed intermolecular regio- and -selective cross-electrophile -butylalkylation of alkynes.通过镍催化炔烃的分子间区域和立体选择性交叉亲电仲丁基烷基化反应实现快速获取仲丁基烷基化烯烃。
Chem Sci. 2022 Mar 30;13(17):4930-4935. doi: 10.1039/d2sc00487a. eCollection 2022 May 4.
6
Stereoselective synthesis of pentasubstituted 1,3-dienes Ni-catalyzed reductive coupling of unsymmetrical internal alkynes.五取代1,3 - 二烯的立体选择性合成:镍催化的不对称内炔还原偶联反应
Chem Sci. 2020 Sep 10;11(37):10204-10211. doi: 10.1039/d0sc04173d.
7
Ni-catalyzed regio- and stereo-defined intermolecular cross-electrophile dialkylation of alkynes without directing group.镍催化炔烃的区域和立体定向分子间交叉亲电二烷基化反应,无需导向基团。
Nat Commun. 2021 Feb 10;12(1):928. doi: 10.1038/s41467-021-21083-w.
8
Synthesis of Tetrasubstituted Alkenes by Tandem Metallacycle Formation/Cross-Electrophile Coupling.通过金属环化/交叉亲电偶联串联合成四取代烯烃。
J Am Chem Soc. 2018 Jun 13;140(23):7074-7078. doi: 10.1021/jacs.8b04637. Epub 2018 May 31.
9
NHC Ligands Tailored for Simultaneous Regio- and Enantiocontrol in Nickel-Catalyzed Reductive Couplings.NHC 配体在镍催化的还原偶联中用于同时控制区域和对映选择性。
J Am Chem Soc. 2017 Jul 12;139(27):9317-9324. doi: 10.1021/jacs.7b04583. Epub 2017 Jul 3.
10
Asymmetric functional organozinc additions to aldehydes catalyzed by 1,1'-bi-2-naphthols (BINOLs).由1,1'-联-2-萘酚(BINOLs)催化的醛的不对称官能团有机锌加成反应。
Acc Chem Res. 2014 May 20;47(5):1523-35. doi: 10.1021/ar500020k. Epub 2014 Apr 16.