• 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

手性螺环膦烷配体在钯催化醛与烯丙醇的不对称烯丙基化反应中的合成与应用

Synthesis and application of chiral spiro phospholane ligand in Pd-catalyzed asymmetric allylation of aldehydes with allylic alcohols.

作者信息

Zhu Shou-Fei, Yang Yun, Wang Li-Xin, Liu Bin, 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

Org Lett. 2005 Jun 9;7(12):2333-5. doi: 10.1021/ol050556x.

DOI:10.1021/ol050556x
PMID:15932191
Abstract

[reaction: see text] A novel chiral monodentate spiro phenylphospholane ligand 4 was prepared from a readily accessible, enantiomerically pure 1,1'-spirobiindane-7,7'-diol in high yield. This ligand has proven to be efficient for Pd-catalyzed enantioselective allylation of aldehydes with allylic alcohols. Aromatic, heteroaromatic, and aliphatic aldehydes gave homoallylic alcohols in good enantioselectivities (up to 83% ee) and excellent anti diastereoselectivities (up to 99:1 dr).

摘要

[反应:见正文] 一种新型手性单齿螺环苯基膦烷配体4由易于获得的对映体纯的1,1'-螺二氢茚-7,7'-二醇高产率制备而成。该配体已被证明在钯催化的醛与烯丙醇的对映选择性烯丙基化反应中是有效的。芳香醛、杂芳醛和脂肪醛能以良好的对映选择性(高达83% ee)和优异的非对映选择性(高达99:1 dr)生成高烯丙醇。

相似文献

1
Synthesis and application of chiral spiro phospholane ligand in Pd-catalyzed asymmetric allylation of aldehydes with allylic alcohols.手性螺环膦烷配体在钯催化醛与烯丙醇的不对称烯丙基化反应中的合成与应用
Org Lett. 2005 Jun 9;7(12):2333-5. doi: 10.1021/ol050556x.
2
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.
3
Synthesis of a new chiral nonracemic C(2)-symmetric 2,2'-bipyridyl ligand and its application in copper(I)-catalyzed enantioselective cyclopropanation reactions.一种新型手性非外消旋C(2)对称2,2'-联吡啶配体的合成及其在铜(I)催化的对映选择性环丙烷化反应中的应用。
Org Lett. 2004 Mar 4;6(5):855-7. doi: 10.1021/ol049853c.
4
Biaryl phosphites: new efficient adaptative ligands for Pd-catalyzed asymmetric allylic substitution reactions.联芳基膦酸酯:用于钯催化不对称烯丙基取代反应的新型高效适应性配体。
Acc Chem Res. 2010 Feb 16;43(2):312-22. doi: 10.1021/ar9002152.
5
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.
6
Synthesis of monodentate chiral spiro phosphonites and the electronic effect of ligand in asymmetric hydrogenation.单齿手性螺环亚磷酸酯的合成及其配体在不对称氢化反应中的电子效应
J Org Chem. 2004 Nov 12;69(23):8157-60. doi: 10.1021/jo049146x.
7
Structurally simple pyridine N-oxides as efficient organocatalysts for the enantioselective allylation of aromatic aldehydes.结构简单的吡啶氮氧化物作为芳香醛对映选择性烯丙基化反应的高效有机催化剂。
J Org Chem. 2006 Feb 17;71(4):1458-63. doi: 10.1021/jo052132m.
8
Synthesis of new monodentate spiro phosphoramidite ligand and its application in Rh-catalyzed asymmetric hydrogenation reactions.新型单齿螺环亚磷酰胺配体的合成及其在铑催化不对称氢化反应中的应用。
Org Lett. 2004 Sep 30;6(20):3565-7. doi: 10.1021/ol048528m.
9
Enantioselective allylation of aldehydes catalyzed by chiral indium(III) complexes immobilized in ionic liquids.离子液体中固定化手性铟(III)配合物催化醛的对映选择性烯丙基化反应。
Chem Commun (Camb). 2005 May 14(18):2345-7. doi: 10.1039/b500086f. Epub 2005 Mar 15.
10
Palladium-catalyzed enantioselective allylic alkylation of thiocarboxylate ions: asymmetric synthesis of allylic thioesters and memory effect/dynamic kinetic resolution of allylic esters.钯催化硫代羧酸根离子的对映选择性烯丙基烷基化反应:烯丙基硫酯的不对称合成及烯丙基酯的记忆效应/动态动力学拆分
J Org Chem. 2004 Jun 11;69(12):4041-52. doi: 10.1021/jo049756x.

引用本文的文献

1
Bis(bicyclo[1.1.1]pentyl)chlorophosphine as a Precursor for the Preparation of Bis(bicyclo[1.1.1]pentyl)phosphines.双(双环[1.1.1]戊基)氯膦作为制备双(双环[1.1.1]戊基)膦的前体。
Org Lett. 2024 Jul 26;26(29):6071-6075. doi: 10.1021/acs.orglett.4c01190. Epub 2024 May 12.
2
Diastereo- and Enantioselective Ruthenium-Catalyzed C-C Coupling of 1-Arylpropynes and Alcohols: Alkynes as Chiral Allylmetal Precursors in Carbonyl -(α-Aryl)allylation.对映选择性和非对映选择性钌催化 1-芳基丙炔与醇的 C-C 偶联反应:炔烃作为手性烯丙基金属前体在羰基-(α-芳基)烯丙基化反应中的应用。
J Am Chem Soc. 2021 Feb 24;143(7):2838-2845. doi: 10.1021/jacs.0c12242. Epub 2021 Feb 8.
3
Enantioselective Catalytic [4+1]-Cyclization of ortho-Hydroxy-para-Quinone Methides with Allenoates.
邻羟基对醌甲基化物与联烯酸酯的对映选择性催化[4+1]环化反应
Chemistry. 2019 Jun 18;25(34):8163-8168. doi: 10.1002/chem.201901784. Epub 2019 May 21.
4
Selection between Diastereomeric Kinetic vs Thermodynamic Carbonyl Binding Modes Enables Enantioselective Iridium-Catalyzed anti-(α-Aryl)allylation of Aqueous Fluoral Hydrate and Difluoroacetaldehyde Ethyl Hemiacetal.对非对映选择性动力学与热力学羰基结合模式的选择使手性铱催化氟醛水合物和二氟乙醛乙基半缩醛的反-(α-芳基)烯丙基化反应成为可能。
J Am Chem Soc. 2018 Aug 1;140(30):9392-9395. doi: 10.1021/jacs.8b05725. Epub 2018 Jul 18.
5
Chiral phosphine-catalyzed tunable cycloaddition reactions of allenoates with benzofuranone-derived olefins for a highly regio-, diastereo- and enantioselective synthesis of spiro-benzofuranones.手性膦催化的丙烯酸酯与苯并呋喃酮衍生烯烃的可调环加成反应,用于高区域、非对映和对映选择性合成螺苯并呋喃酮。
Chem Sci. 2015 Dec 1;6(12):7319-7325. doi: 10.1039/c5sc03135d. Epub 2015 Sep 15.
6
Catalytic Nucleophilic Allylation Driven by the Water-Gas Shift Reaction.水煤气变换反应驱动的催化亲核烯丙基化反应。
J Org Chem. 2018 Jan 5;83(1):23-48. doi: 10.1021/acs.joc.7b02658. Epub 2017 Dec 8.
7
An Expeditious Synthesis of Sialic Acid Derivatives by Copper(I)-Catalyzed Stereodivergent Propargylation of Unprotected Aldoses.铜(I)催化的未保护醛糖的立体发散炔丙基化反应快速合成唾液酸衍生物。
ACS Cent Sci. 2016 Jan 27;2(1):21-6. doi: 10.1021/acscentsci.5b00360. Epub 2016 Jan 4.
8
Phosphine-Catalyzed Doubly Stereoconvergent γ-Additions of Racemic Heterocycles to Racemic Allenoates: The Catalytic Enantioselective Synthesis of Protected α,α-Disubstituted α-Amino Acid Derivatives.膦催化外消旋杂环与外消旋联烯酸酯的双立体汇聚γ-加成反应:受保护的α,α-二取代α-氨基酸衍生物的催化对映选择性合成
J Am Chem Soc. 2015 Jul 29;137(29):9438-42. doi: 10.1021/jacs.5b05528. Epub 2015 Jul 20.
9
Use of a new spirophosphine to achieve catalytic enantioselective [4 + 1] annulations of amines with allenes to generate dihydropyrroles.使用一种新型螺膦实现胺与丙二烯的催化对映选择性[4 + 1]环化反应以生成二氢吡咯。
J Am Chem Soc. 2015 Mar 25;137(11):3803-6. doi: 10.1021/jacs.5b01944. Epub 2015 Mar 17.
10
Catalytic asymmetric C-N bond formation: phosphine-catalyzed intra- and intermolecular γ-addition of nitrogen nucleophiles to allenoates and alkynoates.催化不对称 C-N 键形成:膦催化氮亲核试剂对 allenates 和 alkynoates 的分子内和分子间 γ-加成。
Angew Chem Int Ed Engl. 2013 Feb 25;52(9):2525-8. doi: 10.1002/anie.201208957. Epub 2013 Jan 21.