A Chiral Relay Race: Stereoselective Synthesis of Axially Chiral Biaryl Diketones through Ring-Opening of Optical Dihydrophenan-threne-9,10-diols

We report herein a point-to-axial chirality transfer reaction of optical dihydrophenanthrene-9,10-diols for the synthesis of axially chiral diketones. Two sets of conditions, namely a basic tBuOK/air atmosphere and an acidic NaClO/n-Bu(4)NHSO(4), were developed to oxidatively cleave the C-C bond, re...

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Detalles Bibliográficos
Autores principales: Shi, Lei, Zhu, Jiawei, Hong, Biqiong, Gu, Zhenhua
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10459955/
https://www.ncbi.nlm.nih.gov/pubmed/37630207
http://dx.doi.org/10.3390/molecules28165956
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author Shi, Lei
Zhu, Jiawei
Hong, Biqiong
Gu, Zhenhua
author_facet Shi, Lei
Zhu, Jiawei
Hong, Biqiong
Gu, Zhenhua
author_sort Shi, Lei
collection PubMed
description We report herein a point-to-axial chirality transfer reaction of optical dihydrophenanthrene-9,10-diols for the synthesis of axially chiral diketones. Two sets of conditions, namely a basic tBuOK/air atmosphere and an acidic NaClO/n-Bu(4)NHSO(4), were developed to oxidatively cleave the C-C bond, resulting in the formation of axially chiral biaryl diketones. Finally, brief synthetic applications of the obtained chiral aryl diketones were demonstrated.
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spelling pubmed-104599552023-08-27 A Chiral Relay Race: Stereoselective Synthesis of Axially Chiral Biaryl Diketones through Ring-Opening of Optical Dihydrophenan-threne-9,10-diols Shi, Lei Zhu, Jiawei Hong, Biqiong Gu, Zhenhua Molecules Article We report herein a point-to-axial chirality transfer reaction of optical dihydrophenanthrene-9,10-diols for the synthesis of axially chiral diketones. Two sets of conditions, namely a basic tBuOK/air atmosphere and an acidic NaClO/n-Bu(4)NHSO(4), were developed to oxidatively cleave the C-C bond, resulting in the formation of axially chiral biaryl diketones. Finally, brief synthetic applications of the obtained chiral aryl diketones were demonstrated. MDPI 2023-08-08 /pmc/articles/PMC10459955/ /pubmed/37630207 http://dx.doi.org/10.3390/molecules28165956 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Shi, Lei
Zhu, Jiawei
Hong, Biqiong
Gu, Zhenhua
A Chiral Relay Race: Stereoselective Synthesis of Axially Chiral Biaryl Diketones through Ring-Opening of Optical Dihydrophenan-threne-9,10-diols
title A Chiral Relay Race: Stereoselective Synthesis of Axially Chiral Biaryl Diketones through Ring-Opening of Optical Dihydrophenan-threne-9,10-diols
title_full A Chiral Relay Race: Stereoselective Synthesis of Axially Chiral Biaryl Diketones through Ring-Opening of Optical Dihydrophenan-threne-9,10-diols
title_fullStr A Chiral Relay Race: Stereoselective Synthesis of Axially Chiral Biaryl Diketones through Ring-Opening of Optical Dihydrophenan-threne-9,10-diols
title_full_unstemmed A Chiral Relay Race: Stereoselective Synthesis of Axially Chiral Biaryl Diketones through Ring-Opening of Optical Dihydrophenan-threne-9,10-diols
title_short A Chiral Relay Race: Stereoselective Synthesis of Axially Chiral Biaryl Diketones through Ring-Opening of Optical Dihydrophenan-threne-9,10-diols
title_sort chiral relay race: stereoselective synthesis of axially chiral biaryl diketones through ring-opening of optical dihydrophenan-threne-9,10-diols
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10459955/
https://www.ncbi.nlm.nih.gov/pubmed/37630207
http://dx.doi.org/10.3390/molecules28165956
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