Suppr超能文献

2-氮杂双烯作为手性胺试剂:酮的铜催化对映选择性还原偶联反应合成 1,2-氨基叔醇。

2-Azadienes as Reagents for Preparing Chiral Amines: Synthesis of 1,2-Amino Tertiary Alcohols by Cu-Catalyzed Enantioselective Reductive Couplings with Ketones.

机构信息

Department of Chemistry, Duke University , Durham, North Carolina 27708, United States.

出版信息

J Am Chem Soc. 2018 Jan 17;140(2):598-601. doi: 10.1021/jacs.7b12213. Epub 2018 Jan 4.

Abstract

We introduce a new strategy for synthesis of chiral amines: couplings of α-aminoalkyl nucleophiles generated by enantioselective migratory insertion of 2-azadienes to a Cu-H. In this report, we demonstrate its application in catalytic reductive coupling of 2-azadienes and ketones to furnish 1,2-amino tertiary alcohols with vicinal stereogenic centers.

摘要

我们介绍了一种合成手性胺的新策略

通过对 2-氮杂二烯的对映选择性迁移插入生成的α-氨基烷基亲核试剂与 Cu-H 的偶联。在本报告中,我们证明了其在手性 2-氮杂二烯和酮的催化还原偶联中的应用,以提供具有相邻立体中心的 1,2-氨基叔醇。

相似文献

2
Enantioselective copper-catalyzed reductive coupling of alkenylazaarenes with ketones.
J Am Chem Soc. 2012 May 23;134(20):8428-31. doi: 10.1021/ja3036916. Epub 2012 May 11.
6
Cu-Catalyzed Diastereo- and Enantioselective Reactions of γ,γ-Disubstituted Allyldiboron Compounds with Ketones.
Angew Chem Int Ed Engl. 2020 May 25;59(22):8451-8455. doi: 10.1002/anie.202000675. Epub 2020 Mar 24.
8
2-Azadienes as Enamine Umpolung Synthons for the Preparation of Chiral Amines.
Synlett. 2019 Jul;30(11):1253-1268. doi: 10.1055/s-0037-1611770. Epub 2019 Mar 26.
9
Copper(I) catalyzed asymmetric 1,2-addition of Grignard reagents to α-methyl substituted α,β-unsaturated ketones.
Chem Commun (Camb). 2012 Feb 1;48(10):1478-80. doi: 10.1039/c1cc16725a. Epub 2011 Nov 28.

引用本文的文献

2
Ir-catalyzed reductive amination and transfer hydrogenation of diketones: access to β- and γ-amino alcohols.
RSC Adv. 2024 Nov 29;14(51):38105-38109. doi: 10.1039/d4ra07386j. eCollection 2024 Nov 25.
5
A Neutral PCP Co(I)-Me Pincer Complex as a Catalyst for -Allylic Isomerization with a Broad Substrate Scope.
J Org Chem. 2024 Apr 5;89(7):4319-4325. doi: 10.1021/acs.joc.3c02349. Epub 2024 Mar 23.
6
Intermolecular Hydroalkoxylation and Hydrocarboxylation of 2-Azadienes with High Efficiency.
J Org Chem. 2023 Mar 3;88(5):3277-3281. doi: 10.1021/acs.joc.2c02534. Epub 2023 Feb 21.
8
α-Branched amines through radical coupling with 2-azaallyl anions, redox active esters and alkenes.
Chem Sci. 2022 Mar 3;13(13):3740-3747. doi: 10.1039/d2sc00500j. eCollection 2022 Mar 30.
9
Regio-, Diastereo-, and Enantioselective Decarboxylative Hydroaminoalkylation of Dienol Ethers Enabled by Dual Palladium/Photoredox Catalysis.
Angew Chem Int Ed Engl. 2022 May 9;61(20):e202200105. doi: 10.1002/anie.202200105. Epub 2022 Mar 16.

本文引用的文献

1
Pd-catalyzed asymmetric allylic alkylations C-H activation of -allyl imines with glycinates.
Chem Sci. 2017 Oct 1;8(10):6815-6821. doi: 10.1039/c7sc02899g. Epub 2017 Aug 15.
2
Highly Regio- and Enantioselective Copper-Catalyzed Reductive Hydroxymethylation of Styrenes and 1,3-Dienes with CO.
J Am Chem Soc. 2017 Nov 29;139(47):17011-17014. doi: 10.1021/jacs.7b10149. Epub 2017 Nov 10.
4
Enantioselective CuH-Catalyzed Hydroacylation Employing Unsaturated Carboxylic Acids as Aldehyde Surrogates.
J Am Chem Soc. 2017 Jun 21;139(24):8126-8129. doi: 10.1021/jacs.7b04937. Epub 2017 Jun 6.
5
Catalytic Reductive Synthesis and Direct Derivatization of Unprotected Aminoindoles, Aminopyrroles, and Iminoindolines.
Angew Chem Int Ed Engl. 2017 May 22;56(22):6103-6106. doi: 10.1002/anie.201702310. Epub 2017 Apr 26.
6
Decarboxylative borylation.
Science. 2017 Jun 9;356(6342). doi: 10.1126/science.aam7355. Epub 2017 Apr 13.
8
Nickel-Catalyzed Barton Decarboxylation and Giese Reactions: A Practical Take on Classic Transforms.
Angew Chem Int Ed Engl. 2017 Jan 2;56(1):260-265. doi: 10.1002/anie.201609662. Epub 2016 Dec 16.
9
Decarboxylative Peptide Macrocyclization through Photoredox Catalysis.
Angew Chem Int Ed Engl. 2017 Jan 16;56(3):728-732. doi: 10.1002/anie.201608207. Epub 2016 Nov 17.

文献AI研究员

20分钟写一篇综述,助力文献阅读效率提升50倍。

立即体验

用中文搜PubMed

大模型驱动的PubMed中文搜索引擎

马上搜索

文档翻译

学术文献翻译模型,支持多种主流文档格式。

立即体验