布朗斯特酸催化的串联反应用于非对映选择性合成环丁烷并四氢喹啉羧酸酯。

A Brønsted acid catalyzed tandem reaction for the diastereoselective synthesis of cyclobuta-fused tetrahydroquinoline carboxylic esters.

机构信息

Dipartimento di Scienze Chimiche e Geologiche, Università degli Studi di Cagliari, Complesso Universitario di Monserrato, S.S. 554, Bivio per Sestu, I-09042, Monserrato, Cagliari, Italy.

Dipartimento di Scienze della Vita e dell'Ambiente, Università degli Studi di Cagliari, Via Ospedale 72, 09124, Cagliari, Italy.

出版信息

Org Biomol Chem. 2021 Oct 27;19(41):8912-8916. doi: 10.1039/d1ob01518d.

DOI:10.1039/d1ob01518d

Abstract

A novel Brønsted acid catalyzed tandem reaction provides highly functionalized cyclobuta-fused tetrahydroquinoline carboxylic esters from anilines and 2-alkylenecyclobutanones in good to high yield. During the reaction a dynamic diastereoselective cyclization is achieved, resulting in the formation of three contiguous stereocenters with high stereoselectivity.

摘要

一种新型的布朗斯特酸催化串联反应，可从苯胺和 2-亚烷基环丁酮中高产率得到高官能化的环丁并稠合四氢喹啉羧酸酯。在反应过程中，实现了动态的非对映选择性环化，高立体选择性地形成三个连续的立体中心。

相似文献

1

A Brønsted acid catalyzed tandem reaction for the diastereoselective synthesis of cyclobuta-fused tetrahydroquinoline carboxylic esters.布朗斯特酸催化的串联反应用于非对映选择性合成环丁烷并四氢喹啉羧酸酯。

Org Biomol Chem. 2021 Oct 27;19(41):8912-8916. doi: 10.1039/d1ob01518d.

2

Diastereoselective synthesis of substituted tetrahydroquinoline-4-carboxylic esters by a tandem reduction-reductive amination reaction.通过串联还原-还原胺化反应非对映选择性合成取代的四氢喹啉-4-羧酸酯

J Org Chem. 2001 Apr 20;66(8):2822-7. doi: 10.1021/jo001761n.

3

Catalytic Asymmetric Cascade Cyclization for Constructing Three Contiguous Stereocenters in Pyrrolobenzodiazepine-Based Cyclopentanones.用于在基于吡咯并苯二氮䓬的环戊酮中构建三个相邻立体中心的催化不对称串联环化反应

Org Lett. 2019 Apr 19;21(8):2790-2794. doi: 10.1021/acs.orglett.9b00749. Epub 2019 Apr 1.

4

Diastereoselective Synthesis of Functionalized 5-Amino-3,4-Dihydro-2H-Pyrrole-2-Carboxylic Acid Esters: One-Pot Approach Using Commercially Available Compounds and Benign Solvents.手性 5-氨基-3,4-二氢-2H-吡咯-2-羧酸酯的立体选择性合成：使用商业可得的化合物和良性溶剂的一锅法途径。

Chemistry. 2021 Mar 8;27(14):4573-4577. doi: 10.1002/chem.202005262. Epub 2021 Feb 11.

5

Enantioselective Polyene Cyclization Catalyzed by a Chiral Brønsted Acid.手性 Brønsted 酸催化的对映选择性聚烯环化反应。

Angew Chem Int Ed Engl. 2018 Feb 19;57(8):2115-2119. doi: 10.1002/anie.201711603. Epub 2018 Feb 2.

6

Enantio- and Diastereoselective Synthesis of Functionalized Carbocycles by Cu-Catalyzed Borylative Cyclization of Alkynes with Ketones.通过铜催化的炔烃与酮的硼化环化反应实现官能化碳环的对映选择性和非对映选择性合成。

Org Lett. 2019 Jul 5;21(13):5172-5177. doi: 10.1021/acs.orglett.9b01769. Epub 2019 Jun 14.

7

Enantio- and diastereoselective access to distant stereocenters embedded within tetrahydroxanthenes: utilizing ortho-quinone methides as reactive intermediates in asymmetric Brønsted acid catalysis.对映选择性和非对映选择性地构建四氢蒽酮中远程手性中心：利用邻醌甲醚作为不对称布朗斯特酸催化中的反应中间体。

Angew Chem Int Ed Engl. 2014 Nov 24;53(48):13258-63. doi: 10.1002/anie.201406587. Epub 2014 Oct 6.

8

Tandem beta-enamino ester formation and cyclization with o-alkynyl anilines catalyzed by InBr3: efficient synthesis of beta-(N-indolyl)-alpha,beta-unsaturated esters.三溴化铟催化的串联β-烯胺酯形成及与邻炔基苯胺的环化反应：高效合成β-(N-吲哚基)-α,β-不饱和酯

J Org Chem. 2009 Feb 6;74(3):1418-21. doi: 10.1021/jo802435b.

9

Enantio- and diastereoselective conjugate borylation/Mannich cyclization.对映选择性和非对映选择性共轭硼氢化/曼尼希环化反应。

Chem Sci. 2020 May 18;11(22):5716-5723. doi: 10.1039/d0sc02421j.

10

Direct assembly of aldehydes, amino esters, and anilines into chiral imidazolidines via Brønsted acid catalyzed asymmetric 1,3-dipolar cycloadditions.通过布朗斯特酸催化的不对称 1,3-偶极环加成反应，直接将醛、氨基酯和苯胺组装成手性咪唑烷。

Org Lett. 2008 Dec 4;10(23):5357-60. doi: 10.1021/ol802177s.

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。

用中文搜PubMed

大模型驱动的PubMed中文搜索引擎

文档翻译

学术文献翻译模型，支持多种主流文档格式。