通过协同异硫脲/钯催化实现 α-烷基化吡咯的对映选择性合成。
An enantioselective synthesis of α-alkylated pyrroles via cooperative isothiourea/palladium catalysis.
机构信息
Department of Chemistry, Indiana University, 800 E Kirkwood Ave., Bloomington, IN 47405, USA.
出版信息
Org Biomol Chem. 2019 Feb 13;17(7):1787-1790. doi: 10.1039/c8ob02600a.
Abstract
Herein we describe the direct enantioselective Lewis base/Pd catalysed α-allylation of pyrrole acetic acid esters. This provides high isolated yields of highly enantioenriched products and exhibits broad reaction scope with respect to both reaction partners. The products can be readily elaborated in a manner which points towards potential applications in target directed synthesis.
摘要
在此，我们描述了吡咯乙酸酯的直接对映选择性路易斯碱/Pd 催化的α-烯丙基化反应。该反应提供了高分离收率的高度对映富集产物，并在反应伙伴方面具有广泛的反应范围。产物可以以一种指向在靶向合成中潜在应用的方式进行易于修饰。
相似文献
1
An enantioselective synthesis of α-alkylated pyrroles via cooperative isothiourea/palladium catalysis.
Org Biomol Chem. 2019 Feb 13;17(7):1787-1790. doi: 10.1039/c8ob02600a.
2
Enantioselective α-Allylation of Acyclic Esters Using B(pin)-Substituted Electrophiles: Independent Regulation of Stereocontrol Elements through Cooperative Pd/Lewis Base Catalysis.
Chemistry. 2018 Sep 25;24(54):14378-14381. doi: 10.1002/chem.201803543. Epub 2018 Sep 3.
3
Enantioselective -Allylation of Aryl Acetic Acid Esters via C1-Ammonium Enolate Nucleophiles: Identification of a Broadly Effective Palladium Catalyst for Electron-Deficient Electrophiles.
ACS Catal. 2018 Nov 2;8(11):10537-10544. doi: 10.1021/acscatal.8b03507. Epub 2018 Sep 27.
4
Exploring the Scope of Tandem Palladium and Isothiourea Relay Catalysis for the Synthesis of α-Amino Acid Derivatives.
Molecules. 2020 May 25;25(10):2463. doi: 10.3390/molecules25102463.
5
Traversing Steric Limitations by Cooperative Lewis Base/Palladium Catalysis: An Enantioselective Synthesis of α-Branched Esters Using 2-Substituted Allyl Electrophiles.
Angew Chem Int Ed Engl. 2018 Jun 25;57(26):7800-7803. doi: 10.1002/anie.201803277. Epub 2018 May 18.
6
A Pd-H/Isothiourea Cooperative Catalysis Approach to anti-Aldol Motifs: Enantioselective α-Alkylation of Esters with Oxyallenes.
Angew Chem Int Ed Engl. 2022 Jun 20;61(25):e202201753. doi: 10.1002/anie.202201753. Epub 2022 Apr 20.
7
Cooperative Palladium/Isothiourea Catalyzed Enantioselective Formal (3+2) Cycloaddition of Vinylcyclopropanes and α,β-Unsaturated Esters.
Angew Chem Int Ed Engl. 2022 Jun 20;61(25):e202202621. doi: 10.1002/anie.202202621. Epub 2022 Apr 28.
8
Si-Directed regiocontrol in asymmetric Pd-catalyzed allylic alkylations using C1-ammonium enolate nucleophiles.
Tetrahedron. 2018 Sep 20;74(38):5383-5391. doi: 10.1016/j.tet.2018.04.021. Epub 2018 Apr 10.
9
Enantioselective Syntheses of Strychnos and Chelidonium Alkaloids through Regio- and Stereocontrolled Cooperative Catalysis.
Angew Chem Int Ed Engl. 2020 Sep 28;59(40):17556-17564. doi: 10.1002/anie.202005151. Epub 2020 Aug 11.
10
Cooperative Chiral Lewis Base/Palladium-Catalyzed Asymmetric Syntheses of Methylene-Containing δ-Lactams.
European J Org Chem. 2023 Dec 1;26(45):e202300982. doi: 10.1002/ejoc.202300982. Epub 2023 Nov 9.
引用本文的文献
1
Isothiourea-Catalyzed Enantioselective Functionalisation of Glycine Schiff Base Aryl Esters via 1,6- and 1,4-Additions.
ChemistryEurope. 2023 Jul 3;1(1):e202300015. doi: 10.1002/ceur.202300015. Epub 2023 May 3.
2
Cooperative Chiral Lewis Base/Palladium-Catalyzed Asymmetric Syntheses of Methylene-Containing δ-Lactams.
European J Org Chem. 2023 Dec 1;26(45):e202300982. doi: 10.1002/ejoc.202300982. Epub 2023 Nov 9.
3
Isothiourea-Catalyzed Enantioselective Michael Addition of Malonates to α,β-Unsaturated Aryl Esters.
Org Lett. 2022 Jun 10;24(22):4040-4045. doi: 10.1021/acs.orglett.2c01486. Epub 2022 Jun 2.
4
Cooperative Palladium/Isothiourea Catalyzed Enantioselective Formal (3+2) Cycloaddition of Vinylcyclopropanes and α,β-Unsaturated Esters.
Angew Chem Int Ed Engl. 2022 Jun 20;61(25):e202202621. doi: 10.1002/anie.202202621. Epub 2022 Apr 28.
5
Recent progress in asymmetric synergistic catalysis - the judicious combination of selected chiral aminocatalysts with achiral metal catalysts.
Org Biomol Chem. 2022 Apr 6;20(14):2764-2778. doi: 10.1039/d2ob00025c.
6
Isothiourea-Catalyzed Enantioselective α-Alkylation of Esters via 1,6-Conjugate Addition to -Quinone Methides.
Molecules. 2021 Oct 20;26(21):6333. doi: 10.3390/molecules26216333.
7
Catalytic enantioselective synthesis of 1,4-dihydropyridines the addition of C(1)-ammonium enolates to pyridinium salts.
Chem Sci. 2021 Aug 6;12(36):12001-12011. doi: 10.1039/d1sc03860e. eCollection 2021 Sep 22.
8
Recent Advances in Enantioselective Pd-Catalyzed Allylic Substitution: From Design to Applications.
Chem Rev. 2021 Apr 28;121(8):4373-4505. doi: 10.1021/acs.chemrev.0c00736. Epub 2021 Mar 19.
9
Generation and Reactivity of C(1)-Ammonium Enolates by Using Isothiourea Catalysis.
Chemistry. 2021 Jan 21;27(5):1533-1555. doi: 10.1002/chem.202002059. Epub 2020 Nov 10.
10
A Regio- and Stereodivergent Synthesis of Homoallylic Amines by a One-Pot Cooperative-Catalysis-Based Allylic Alkylation/Hofmann Rearrangement Strategy.
Angew Chem Int Ed Engl. 2019 Jul 29;58(31):10521-10527. doi: 10.1002/anie.201905426. Epub 2019 Jun 28.
本文引用的文献
1
Enantioselective -Allylation of Aryl Acetic Acid Esters via C1-Ammonium Enolate Nucleophiles: Identification of a Broadly Effective Palladium Catalyst for Electron-Deficient Electrophiles.
ACS Catal. 2018 Nov 2;8(11):10537-10544. doi: 10.1021/acscatal.8b03507. Epub 2018 Sep 27.
2
Si-Directed regiocontrol in asymmetric Pd-catalyzed allylic alkylations using C1-ammonium enolate nucleophiles.
Tetrahedron. 2018 Sep 20;74(38):5383-5391. doi: 10.1016/j.tet.2018.04.021. Epub 2018 Apr 10.
3
Isothiourea-Catalyzed Enantioselective Functionalization of 2-Pyrrolyl Acetic Acid: Two-Step Synthesis of Stereodefined Dihydroindolizinones.
Org Lett. 2018 Sep 7;20(17):5482-5485. doi: 10.1021/acs.orglett.8b02423. Epub 2018 Aug 24.
4
Enantioselective α-Allylation of Acyclic Esters Using B(pin)-Substituted Electrophiles: Independent Regulation of Stereocontrol Elements through Cooperative Pd/Lewis Base Catalysis.
Chemistry. 2018 Sep 25;24(54):14378-14381. doi: 10.1002/chem.201803543. Epub 2018 Sep 3.
5
Enantioselective α-Benzylation of Acyclic Esters Using π-Extended Electrophiles.
Angew Chem Int Ed Engl. 2018 Sep 10;57(37):12102-12105. doi: 10.1002/anie.201806742. Epub 2018 Aug 20.
6
Traversing Steric Limitations by Cooperative Lewis Base/Palladium Catalysis: An Enantioselective Synthesis of α-Branched Esters Using 2-Substituted Allyl Electrophiles.
Angew Chem Int Ed Engl. 2018 Jun 25;57(26):7800-7803. doi: 10.1002/anie.201803277. Epub 2018 May 18.
7
Elucidating the Role of the Boronic Esters in the Suzuki-Miyaura Reaction: Structural, Kinetic, and Computational Investigations.
J Am Chem Soc. 2018 Mar 28;140(12):4401-4416. doi: 10.1021/jacs.8b00400. Epub 2018 Mar 15.
8
Lewis Base/Copper Cooperatively Catalyzed Asymmetric α-Amination of Esters with Diaziridinone.
J Am Chem Soc. 2018 Mar 7;140(9):3177-3180. doi: 10.1021/jacs.7b12628. Epub 2018 Feb 7.
9
Interrogating Pd(II) Anion Metathesis Using a Bifunctional Chemical Probe: A Transmetalation Switch.
J Am Chem Soc. 2018 Jan 10;140(1):126-130. doi: 10.1021/jacs.7b11180. Epub 2017 Dec 22.
10
Tandem Palladium and Isothiourea Relay Catalysis: Enantioselective Synthesis of α-Amino Acid Derivatives via Allylic Amination and [2,3]-Sigmatropic Rearrangement.
J Am Chem Soc. 2017 Aug 30;139(34):11895-11902. doi: 10.1021/jacs.7b05619. Epub 2017 Aug 22.
Zotero 插件