Suppr超能文献

手性联烯酮与烯烃的立体选择性[2+2]环加成反应:在苯并环丁烯和内型双环二烯酸合成中的应用

Stereoselective [2+2]-Cycloadditions of chiral allenic ketones and alkenes: Applications towards the synthesis of benzocyclobutenes and endiandric acids.

作者信息

Guo Renyu, Witherspoon Brittany P, Brown M Kevin

机构信息

Indiana University, Department of Chemistry, 800 E. Kirkwood Ave., Bloomington, IN, 47405, USA.

出版信息

Tetrahedron. 2022 Sep 10;122. doi: 10.1016/j.tet.2022.132932. Epub 2022 Aug 8.

Abstract

Cyclobutanes are important motifs that have found utility in many contexts. Prior work has demonstrated an enantioselective isomerization/stereoselective [2 + 2] as a means to access bicyclo [4.2.0] octanes. Herein, the utility of this method is demonstrated towards the synthesis of benzocyclobutenes and a key intermediate towards the endiandric acids.

摘要

环丁烷是一类重要的结构单元,在许多领域都有应用。先前的研究表明,对映选择性异构化/立体选择性[2 + 2]反应是制备双环[4.2.0]辛烷的一种方法。本文展示了该方法在合成苯并环丁烯以及合成对映二酸关键中间体方面的应用。

相似文献

2
Lewis Acid-Promoted [2 + 2] Cycloadditions of Allenes and Ketenes: Versatile Methods for Natural Product Synthesis.
Acc Chem Res. 2023 Aug 15;56(16):2253-2264. doi: 10.1021/acs.accounts.3c00334. Epub 2023 Aug 4.
4
Cyclobutane and cyclobutene synthesis: catalytic enantioselective [2+2] cycloadditions.
Angew Chem Int Ed Engl. 2015 Oct 5;54(41):11918-28. doi: 10.1002/anie.201502815. Epub 2015 Sep 2.
5
Phosphine-Catalyzed [4+2] Cycloadditions of Allenic Ketones: Enantioselective Synthesis of Functionalized Tetrahydropyridines.
Chem Asian J. 2019 Oct 1;14(19):3409-3413. doi: 10.1002/asia.201901104. Epub 2019 Sep 18.
6
Stereoselective nickel-catalyzed [2+2] cycloadditions of ene-allenes.
Angew Chem Int Ed Engl. 2015 Apr 27;54(18):5447-50. doi: 10.1002/anie.201411737. Epub 2015 Mar 10.
7
Thioallenoates in Catalytic Enantioselective [2+2]-Cycloadditions with Unactivated Alkenes.
Tetrahedron. 2019 Jun 14;75(24):3265-3271. doi: 10.1016/j.tet.2019.04.028. Epub 2019 Apr 25.
8
Exploiting [2+2] cycloaddition chemistry: achievements with allenes.
Chem Soc Rev. 2010 Feb;39(2):783-816. doi: 10.1039/b913749a. Epub 2009 Oct 22.

引用本文的文献

1
Lewis Acid-Promoted [2 + 2] Cycloadditions of Allenes and Ketenes: Versatile Methods for Natural Product Synthesis.
Acc Chem Res. 2023 Aug 15;56(16):2253-2264. doi: 10.1021/acs.accounts.3c00334. Epub 2023 Aug 4.

本文引用的文献

1
Chiral Photocatalyst Structures in Asymmetric Photochemical Synthesis.
Chem Rev. 2022 Jan 26;122(2):1654-1716. doi: 10.1021/acs.chemrev.1c00467. Epub 2021 Oct 4.
2
Total synthesis of endiandric acid J and beilcyclone A from cyclooctatetraene.
Chem Sci. 2020 Jul 29;11(35):9421-9425. doi: 10.1039/d0sc03073b.
3
3-(Methoxycarbonyl)Cyclobutenone as a Reactive Dienophile in Enantioselective Diels-Alder Reactions Catalyzed by Chiral Oxazaborolidinium Ions.
Angew Chem Int Ed Engl. 2021 Feb 23;60(9):4609-4613. doi: 10.1002/anie.202014308. Epub 2021 Jan 7.
4
Thioallenoates in Catalytic Enantioselective [2+2]-Cycloadditions with Unactivated Alkenes.
Tetrahedron. 2019 Jun 14;75(24):3265-3271. doi: 10.1016/j.tet.2019.04.028. Epub 2019 Apr 25.
5
Enantioselective Synthesis of (+)-Hippolide J and Reevaluation of Antifungal Activity.
Org Lett. 2020 Oct 2;22(19):7743-7746. doi: 10.1021/acs.orglett.0c02979. Epub 2020 Sep 24.
6
Evolution of a Strategy for the Enantioselective Synthesis of (-)-Cajanusine.
J Am Chem Soc. 2020 Mar 18;142(11):5002-5006. doi: 10.1021/jacs.0c00359. Epub 2020 Mar 9.
7
Allenoates in Enantioselective [2+2] Cycloadditions: From a Mechanistic Curiosity to a Stereospecific Transformation.
J Am Chem Soc. 2018 Nov 21;140(46):15943-15949. doi: 10.1021/jacs.8b10008. Epub 2018 Nov 5.
8
Synthesis of (-)-Hebelophyllene E: An Entry to Geminal Dimethyl-Cyclobutanes by [2+2] Cycloaddition of Alkenes and Allenoates.
Angew Chem Int Ed Engl. 2018 Apr 16;57(17):4647-4651. doi: 10.1002/anie.201801110. Epub 2018 Mar 24.
9
Unified total synthesis of the natural products endiandric acid A, kingianic acid E, and kingianins A, D, and F.
Chem Sci. 2015 Jul 1;6(7):3886-3890. doi: 10.1039/c5sc00794a. Epub 2015 May 7.

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