Suppr超能文献

钯催化酰基 C-O 键活化用于 α-亚甲基-β-内酰胺与胺的选择性开环反应。

Pd-Catalyzed Acyl C-O Bond Activation for Selective Ring-Opening of α-Methylene-β-lactones with Amines.

机构信息

Department of Chemistry, University of Connecticut , Storrs, Connecticut 06269-3060, United States.

出版信息

Org Lett. 2017 Apr 21;19(8):1966-1969. doi: 10.1021/acs.orglett.7b00494. Epub 2017 Apr 4.

Abstract

A Pd-catalyzed ring-opening of β-lactones with various types of amines (primary, secondary, and aryl) to provide β-hydroxy amides with excellent selectivity toward acyl C-O bond cleavage is reported. The utility of this protocol is demonstrated in an asymmetric kinetic resolution providing enantioenriched α-methylene-β-lactones.

摘要

报道了一种钯催化的β-内酰胺与各种类型的胺(伯胺、仲胺和芳胺)的开环反应,该反应对酰基 C-O 键的断裂具有极好的选择性,生成了β-羟基酰胺。该方法的实用性通过不对称动力学拆分提供了手性富集的α-亚甲基-β-内酰胺得到了证明。

相似文献

引用本文的文献

5
Nickel-Catalyzed Decarbonylative Amination of Carboxylic Acid Esters.镍催化羧酸酯的脱羰基胺化反应。
J Am Chem Soc. 2020 Apr 1;142(13):5918-5923. doi: 10.1021/jacs.9b13531. Epub 2020 Mar 24.

本文引用的文献

1
Kinetic and Theoretical Studies of Beta-Lactone Reactivity-A Quantitative Scale for Biological Application.
Chempluschem. 2015 Nov;80(11):1673-1679. doi: 10.1002/cplu.201500246. Epub 2015 Jul 16.
2
Palladium-Catalyzed Suzuki-Miyaura Coupling of Aryl Esters.钯催化的芳基酯的铃木-宫浦偶联反应。
J Am Chem Soc. 2017 Jan 25;139(3):1311-1318. doi: 10.1021/jacs.6b12329. Epub 2017 Jan 11.
4
Nickel-Catalyzed Activation of Acyl C-O Bonds of Methyl Esters.镍催化的甲酯酰基C-O键活化
Angew Chem Int Ed Engl. 2016 Feb 18;55(8):2810-4. doi: 10.1002/anie.201511486. Epub 2016 Jan 25.
5
Recent Applications of Oxetanes in the Synthesis of Heterocyclic Compounds.
J Org Chem. 2015 Sep 4;80(17):8489-95. doi: 10.1021/acs.joc.5b01255. Epub 2015 Aug 19.
7
Pt-catalyzed rearrangement of oxaspirohexanes to 3-methylenetetrahydrofurans: scope and mechanism.
J Org Chem. 2015 May 15;80(10):5196-209. doi: 10.1021/acs.joc.5b00604. Epub 2015 May 6.

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