Suppr超能文献

高价碘(III)试剂促进的不对称氧化去芳构化反应:合理催化剂设计的契机?

Asymmetric oxidative dearomatizations promoted by hypervalent iodine(III) reagents: an opportunity for rational catalyst design?

作者信息

Harned Andrew M

机构信息

Department of Chemistry, University of Minnesota-Twin Cities, 207 Pleasant St SE, Minneapolis, Minnesota 55455, United States.

出版信息

Tetrahedron Lett. 2014 Aug 20;55(34):4681-4689. doi: 10.1016/j.tetlet.2014.06.051.

Abstract

The use of and λ- and λ-iodanes in the oxidative dearomatization of phenols is a well-established and general procedure for the construction of cyclohexadienone structures. However, their use in asymmetric dearomatization reactions is quite underdeveloped and, despite work by several research groups over the past several years, a general chiral aryl iodide catalyst has yet to emerge. This article will serve to highlight the significant progress that has been made in this area and will reveal some of deficiencies in the literature that the author believes may be hindering further progress.

摘要

在酚类的氧化去芳构化反应中使用λ-碘烷和λ-碘化物是构建环己二烯酮结构的一种成熟且通用的方法。然而,它们在不对称去芳构化反应中的应用尚不完善,尽管过去几年有几个研究小组开展了相关工作,但通用的手性芳基碘化物催化剂仍未出现。本文旨在突出该领域已取得的重大进展,并揭示文献中作者认为可能阻碍进一步发展的一些不足之处。

相似文献

2
Asymmetric Direct/Stepwise Dearomatization Reactions Involving Hypervalent Iodine Reagents.
Chem Asian J. 2022 Feb 14;17(4):e202101115. doi: 10.1002/asia.202101115. Epub 2021 Dec 7.
3
Asymmetric hydroxylative phenol dearomatization promoted by chiral binaphthylic and biphenylic iodanes.
Angew Chem Int Ed Engl. 2014 Sep 8;53(37):9860-4. doi: 10.1002/anie.201403571. Epub 2014 Jul 22.
5
Chiral Ligands in Hypervalent Iodine Compounds: Synthesis and Structures of Binaphthyl-Based λ -Iodanes.
Chemistry. 2022 Jan 24;28(5):e202103623. doi: 10.1002/chem.202103623. Epub 2021 Dec 16.
6
Enantioselective Phenolic α-Oxidation Using HO via an Unusual Double Dearomatization Mechanism.
J Am Chem Soc. 2019 Feb 13;141(6):2645-2651. doi: 10.1021/jacs.8b13006. Epub 2019 Jan 30.
8
A Triazole-Substituted Aryl Iodide with Omnipotent Reactivity in Enantioselective Oxidations.
Angew Chem Int Ed Engl. 2020 Jan 20;59(4):1479-1484. doi: 10.1002/anie.201912023. Epub 2019 Dec 12.
9
Asymmetric Oxidative Cycloetherification of Naphtholic Alcohols.
Chemistry. 2017 Apr 3;23(19):4542-4546. doi: 10.1002/chem.201700667. Epub 2017 Mar 15.
10
λ - and λ -Iodanes: Substituent Effects and Pseudorotation/Hypervalent Twisting.
Chemistry. 2023 Jun 19;29(34):e202203997. doi: 10.1002/chem.202203997. Epub 2023 May 8.

引用本文的文献

1
Oxidative Dearomatization of PLP in Thiamin Pyrimidine Biosynthesis in .
J Am Chem Soc. 2023 Mar 1;145(8):4421-4430. doi: 10.1021/jacs.2c08560. Epub 2023 Feb 20.
3
New Strategy To Access Enantioenriched Cyclohexadienones: Kinetic Resolution of -Quinols by Organocatalytic Thiol-Michael Addition Reactions.
ACS Omega. 2018 Nov 14;3(11):15492-15500. doi: 10.1021/acsomega.8b01787. eCollection 2018 Nov 30.
5
Enantioselective dioxytosylation of styrenes using lactate-based chiral hypervalent iodine(III).
Beilstein J Org Chem. 2018 Mar 20;14:659-663. doi: 10.3762/bjoc.14.53. eCollection 2018.
7
Asymmetric transformations of achiral 2,5-cyclohexadienones.
Tetrahedron. 2014 Dec 23;70(51):9571-9585. doi: 10.1016/j.tet.2014.07.081.

本文引用的文献

1
Reactivity of hydroxy- and aquo(hydroxy)-λ3-iodane-crown ether complexes.
Chemistry. 2014 Apr 25;20(18):5447-53. doi: 10.1002/chem.201304961. Epub 2014 Mar 18.
2
Ortho-dearomatization of phenols creating all-carbon spiro-bicycles.
Org Lett. 2013 Aug 16;15(16):4046-9. doi: 10.1021/ol401863k. Epub 2013 Aug 2.
3
Hydrogen bonding and alcohol effects in asymmetric hypervalent iodine catalysis: enantioselective oxidative dearomatization of phenols.
Angew Chem Int Ed Engl. 2013 Aug 26;52(35):9215-8. doi: 10.1002/anie.201303559. Epub 2013 Jul 19.
4
Direct detection and reactivity of the short-lived phenyloxenium ion.
J Am Chem Soc. 2013 Jun 19;135(24):9078-82. doi: 10.1021/ja403370k. Epub 2013 Jun 7.
5
Stereoselective rearrangements with chiral hypervalent iodine reagents.
Angew Chem Int Ed Engl. 2013 Jul 1;52(27):7018-22. doi: 10.1002/anie.201302358. Epub 2013 May 7.
6
Pd-catalyzed asymmetric β-hydride elimination en route to chiral allenes.
J Am Chem Soc. 2013 Apr 3;135(13):4970-3. doi: 10.1021/ja401606e. Epub 2013 Mar 19.
7
Chiral aryl iodide catalysts for the enantioselective synthesis of para-quinols.
Chem Commun (Camb). 2013 Apr 14;49(29):3001-3. doi: 10.1039/c3cc00013c.
8
Asymmetric dearomatizing spirolactonization of naphthols catalyzed by spirobiindane-based chiral hypervalent iodine species.
J Am Chem Soc. 2013 Mar 20;135(11):4558-66. doi: 10.1021/ja401074u. Epub 2013 Mar 7.
10
Catalytic asymmetric dearomatization reactions.
Angew Chem Int Ed Engl. 2012 Dec 14;51(51):12662-86. doi: 10.1002/anie.201204822. Epub 2012 Dec 3.

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