Palladium-Catalyzed Stereoselective Construction of 1,3-Stereocenters Displaying Axial and Central Chirality via Asymmetric Alkylations

The concurrent construction of 1,3-stereocenters remains a challenge. Herein, we report the development of stereoselective union of a point chiral center with allenyl axial chirality in 1,3-position by Pd-catalyzed asymmetric allenylic alkylation between racemic allenyl carbonates and indanone-deriv...

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Autores principales: Xue, Aiqi, Wei, Xingfu, Huang, Yue, Qu, Jingping, Wang, Baomin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10096308/
https://www.ncbi.nlm.nih.gov/pubmed/37049689
http://dx.doi.org/10.3390/molecules28072927
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author Xue, Aiqi
Wei, Xingfu
Huang, Yue
Qu, Jingping
Wang, Baomin
author_facet Xue, Aiqi
Wei, Xingfu
Huang, Yue
Qu, Jingping
Wang, Baomin
author_sort Xue, Aiqi
collection PubMed
description The concurrent construction of 1,3-stereocenters remains a challenge. Herein, we report the development of stereoselective union of a point chiral center with allenyl axial chirality in 1,3-position by Pd-catalyzed asymmetric allenylic alkylation between racemic allenyl carbonates and indanone-derived β-ketoesters. Various target products bearing a broad range of functional groups were afforded in high yield (up to 99%) with excellent enantioselectivities (up to 98% ee) and good diastereoselectivities (up to 13:1 dr).
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spelling pubmed-100963082023-04-13 Palladium-Catalyzed Stereoselective Construction of 1,3-Stereocenters Displaying Axial and Central Chirality via Asymmetric Alkylations Xue, Aiqi Wei, Xingfu Huang, Yue Qu, Jingping Wang, Baomin Molecules Article The concurrent construction of 1,3-stereocenters remains a challenge. Herein, we report the development of stereoselective union of a point chiral center with allenyl axial chirality in 1,3-position by Pd-catalyzed asymmetric allenylic alkylation between racemic allenyl carbonates and indanone-derived β-ketoesters. Various target products bearing a broad range of functional groups were afforded in high yield (up to 99%) with excellent enantioselectivities (up to 98% ee) and good diastereoselectivities (up to 13:1 dr). MDPI 2023-03-24 /pmc/articles/PMC10096308/ /pubmed/37049689 http://dx.doi.org/10.3390/molecules28072927 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
Xue, Aiqi
Wei, Xingfu
Huang, Yue
Qu, Jingping
Wang, Baomin
Palladium-Catalyzed Stereoselective Construction of 1,3-Stereocenters Displaying Axial and Central Chirality via Asymmetric Alkylations
title Palladium-Catalyzed Stereoselective Construction of 1,3-Stereocenters Displaying Axial and Central Chirality via Asymmetric Alkylations
title_full Palladium-Catalyzed Stereoselective Construction of 1,3-Stereocenters Displaying Axial and Central Chirality via Asymmetric Alkylations
title_fullStr Palladium-Catalyzed Stereoselective Construction of 1,3-Stereocenters Displaying Axial and Central Chirality via Asymmetric Alkylations
title_full_unstemmed Palladium-Catalyzed Stereoselective Construction of 1,3-Stereocenters Displaying Axial and Central Chirality via Asymmetric Alkylations
title_short Palladium-Catalyzed Stereoselective Construction of 1,3-Stereocenters Displaying Axial and Central Chirality via Asymmetric Alkylations
title_sort palladium-catalyzed stereoselective construction of 1,3-stereocenters displaying axial and central chirality via asymmetric alkylations
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10096308/
https://www.ncbi.nlm.nih.gov/pubmed/37049689
http://dx.doi.org/10.3390/molecules28072927
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