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烯丙基烷基化酮烯醇盐。

The Allylic Alkylation of Ketone Enolates.

机构信息

Organic Chemistry I, Saarland University, Campus C4.2, 66123, Saarbrücken, Germany.

出版信息

ChemistryOpen. 2020 Sep 10;9(9):929-952. doi: 10.1002/open.202000175. eCollection 2020 Sep.

DOI:10.1002/open.202000175
PMID:32953384
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7482671/
Abstract

The palladium-catalyzed allylic alkylation of non-stabilized ketone enolates was thought for a long time to be not as efficient as the analogous reactions of stabilized enolates, e. g. of malonates and β-ketoesters. The field has experienced a rapid development during the last two decades, with a range of new, highly efficient protocols evolved. In this review, the early developments as well as current methods and applications of palladium-catalyzed ketone enolate allylations will be discussed.

摘要

钯催化的非稳定酮烯醇化物的烯丙基烷基化反应长期以来被认为不如类似的稳定烯醇化物反应（例如丙二酸酯和β-酮酯）有效。在过去的二十年中，该领域发展迅速，出现了一系列新的、高效的方法。本文将讨论钯催化酮烯醇化物烯丙基烷基化的早期发展以及当前的方法和应用。

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Chemistry. 2004 Dec 17;11(1):174-84. doi: 10.1002/chem.200400666.
3
Palladium-catalyzed decarboxylative asymmetric allylic alkylation of enol carbonates.钯催化的烯醇碳酸酯的脱羧不对称烯丙基烷基化反应。
J Am Chem Soc. 2009 Dec 30;131(51):18343-57. doi: 10.1021/ja9053948.
4
Development of (trimethylsilyl)ethyl ester protected enolates and applications in palladium-catalyzed enantioselective allylic alkylation: intermolecular cross-coupling of functionalized electrophiles.（三甲基硅基）乙酯保护烯醇化物的开发及其在钯催化的对映选择性烯丙基烷基化反应中的应用：功能化亲电试剂的分子间交叉偶联。
Org Lett. 2014 May 2;16(9):2314-7. doi: 10.1021/ol500355z. Epub 2014 Apr 11.
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Palladium-catalyzed asymmetric allylic alpha-alkylation of acyclic ketones.钯催化的无环酮的不对称烯丙基α-烷基化反应
J Am Chem Soc. 2005 Dec 14;127(49):17180-1. doi: 10.1021/ja055968f.
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Stereoselective palladium-catalyzed allylic alkylations of peptide amide enolates.肽酰胺烯醇化物的立体选择性钯催化烯丙基烷基化反应。
Org Biomol Chem. 2011 Feb 7;9(3):872-80. doi: 10.1039/c0ob00628a. Epub 2010 Dec 1.
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Stereoselective Allylic Alkylations of Amino Ketones and Their Application in the Synthesis of Highly Functionalized Piperidines.手性烯丙基烷基化的氨基酮及其在手性哌啶高官能团化合成中的应用。
Chemistry. 2020 Mar 9;26(14):3181-3188. doi: 10.1002/chem.202000051. Epub 2020 Feb 21.
8
Diastereo- and enantioselective iridium-catalyzed allylation of cyclic ketone enolates: synergetic effect of ligands and barium enolates.环酮烯醇盐的非对映和对映选择性铱催化烯丙基化反应：配体与烯醇钡盐的协同效应
J Am Chem Soc. 2014 Nov 12;136(45):15825-8. doi: 10.1021/ja506500u. Epub 2014 Oct 30.
9
Highly stereoselective modifications of peptides via Pd-catalyzed allylic alkylation of internal peptide amide enolates.通过 Pd 催化的内部肽酰胺烯醇化物的烯丙基烷基化反应实现高对映选择性修饰肽。
Org Biomol Chem. 2012 Oct 3;10(41):8268-75. doi: 10.1039/c2ob26351c.
10
Asymmetric allylic alkylation of ketone enolates: an asymmetric Claisen surrogate.酮烯醇盐的不对称烯丙基烷基化：一种不对称克莱森替代反应。
Org Lett. 2004 Oct 28;6(22):4113-5. doi: 10.1021/ol048149t.

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Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Protected Benzoin-Derived Enol Carbonates.钯催化的受保护苯偶姻衍生的烯醇碳酸酯的对映选择性脱羧烯丙基烷基化反应
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Stereoselective Allylic Alkylations of Amino Ketones and Their Application in the Synthesis of Highly Functionalized Piperidines.手性烯丙基烷基化的氨基酮及其在手性哌啶高官能团化合成中的应用。
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Unified Enantioselective, Convergent Synthetic Approach toward the Furanobutenolide-Derived Polycyclic Norcembranoid Diterpenes: Synthesis of a Series of Ineleganoloids by Oxidation-State Manipulation of the Carbocyclic Core.
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Copper(I)-catalyzed asymmetric alkylation of α-imino-esters.铜（I）催化的α-亚氨基酯不对称烷基化反应。
Nat Commun. 2023 Apr 17;14(1):2187. doi: 10.1038/s41467-023-37967-y.
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A Catalytic Method for the Enantioselective Synthesis of α-Quaternary Ketones, α-Ketoesters and Aldehydes.一种用于α-季碳酮、α-酮酯和醛的对映选择性合成的催化方法。
Angew Chem Int Ed Engl. 2023 Apr 24;62(18):e202215855. doi: 10.1002/anie.202215855. Epub 2023 Jan 25.
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Enantioselective Formation of Quaternary Centers by Allylic Alkylation with First-Row Transition-Metal Catalysts.手性过渡金属催化的烯丙基烷基化反应构建季碳中心。
Chem Rev. 2021 Apr 14;121(7):4084-4099. doi: 10.1021/acs.chemrev.0c01115. Epub 2021 Feb 11.
统一对映选择性、会聚合成方法合成呋喃丁烯醇衍生的多环诺碳烯二萜：通过碳环核心氧化态调控合成一系列 Ineleganoloids。
J Org Chem. 2019 Jun 21;84(12):7722-7746. doi: 10.1021/acs.joc.9b00635. Epub 2019 Jun 10.
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Short Enantioselective Formal Synthesis of (-)-Platencin.（-）-普拉替尼的短对映选择性形式合成
Synthesis (Stuttg). 2018 Nov;50(22):4359-4368. doi: 10.1055/s-0037-1610437. Epub 2018 Jul 23.
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Iridium-Catalyzed Enantioselective Allylation of Aryl Enamides and Enecarbamates.铱催化芳基烯酰胺和烯基氨基甲酸酯的对映选择性烯丙基化反应。
Org Lett. 2019 Apr 5;21(7):2449-2452. doi: 10.1021/acs.orglett.9b00764. Epub 2019 Mar 21.
6
Iridium-Catalyzed Asymmetric Allylic Substitution Reactions.铱催化的不对称烯丙基取代反应。
Chem Rev. 2019 Feb 13;119(3):1855-1969. doi: 10.1021/acs.chemrev.8b00506. Epub 2018 Dec 24.
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Synthesis of Chiral Nonracemic α-Difluoromethylthio Compounds with Tetrasubstituted Stereogenic Centers via a Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation.通过钯催化的脱羧不对称烯丙基烷基化反应合成具有四取代立体中心的手性非外消旋α-二氟甲基硫化合物。
Org Lett. 2018 Nov 16;20(22):7044-7048. doi: 10.1021/acs.orglett.8b02998. Epub 2018 Nov 8.
8
Enol Acetates: Versatile Substrates for the Enantioselective Intermolecular Tsuji Allylation.烯醇醋酸酯：用于对映选择性分子间辻烯丙基化反应的多功能底物
J Am Chem Soc. 2018 Nov 28;140(47):16152-16158. doi: 10.1021/jacs.8b08746. Epub 2018 Nov 13.
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Palladium-Catalyzed Enantioselective C-C Cross-Coupling for the Synthesis of (Poly)fluorinated Chiral Building Blocks.钯催化的对映选择性 C-C 交叉偶联反应在（多）氟代手性砌块合成中的应用。
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