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Asymmetric synthesis of chiral cycloalkenone derivatives via palladium catalysis

The palladium-catalyzed oxidative desymmetrization of meso-dibenzoates yields γ-benzoyloxy cycloalkenones in good yields and with excellent levels of enantioselectivity. These compounds serve as precursors to a broad range of substituted cycloalkenones, including well-established synthetic building...

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Detalles Bibliográficos
Autores principales: Trost, Barry M., Masters, James T., Lumb, Jean-Philip, Fateen, Dahlia
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3992253/
https://www.ncbi.nlm.nih.gov/pubmed/24761221
http://dx.doi.org/10.1039/c3sc53250j
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author Trost, Barry M.
Masters, James T.
Lumb, Jean-Philip
Fateen, Dahlia
author_facet Trost, Barry M.
Masters, James T.
Lumb, Jean-Philip
Fateen, Dahlia
author_sort Trost, Barry M.
collection PubMed
description The palladium-catalyzed oxidative desymmetrization of meso-dibenzoates yields γ-benzoyloxy cycloalkenones in good yields and with excellent levels of enantioselectivity. These compounds serve as precursors to a broad range of substituted cycloalkenones, including well-established synthetic building blocks and elaborated cycloalkanone derivatives. The ability to prepare both enantiomers of the oxidative desymmetrization products enables a unified strategy toward stereochemically diverse epoxyquinoid natural products.
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spelling pubmed-39922532015-03-05 Asymmetric synthesis of chiral cycloalkenone derivatives via palladium catalysis Trost, Barry M. Masters, James T. Lumb, Jean-Philip Fateen, Dahlia Chem Sci Chemistry The palladium-catalyzed oxidative desymmetrization of meso-dibenzoates yields γ-benzoyloxy cycloalkenones in good yields and with excellent levels of enantioselectivity. These compounds serve as precursors to a broad range of substituted cycloalkenones, including well-established synthetic building blocks and elaborated cycloalkanone derivatives. The ability to prepare both enantiomers of the oxidative desymmetrization products enables a unified strategy toward stereochemically diverse epoxyquinoid natural products. Royal Society of Chemistry 2014-04-03 2014-01-27 /pmc/articles/PMC3992253/ /pubmed/24761221 http://dx.doi.org/10.1039/c3sc53250j Text en This journal is © The Royal Society of Chemistry 2014 http://creativecommons.org/licenses/by/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License (http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Trost, Barry M.
Masters, James T.
Lumb, Jean-Philip
Fateen, Dahlia
Asymmetric synthesis of chiral cycloalkenone derivatives via palladium catalysis
title Asymmetric synthesis of chiral cycloalkenone derivatives via palladium catalysis
title_full Asymmetric synthesis of chiral cycloalkenone derivatives via palladium catalysis
title_fullStr Asymmetric synthesis of chiral cycloalkenone derivatives via palladium catalysis
title_full_unstemmed Asymmetric synthesis of chiral cycloalkenone derivatives via palladium catalysis
title_short Asymmetric synthesis of chiral cycloalkenone derivatives via palladium catalysis
title_sort asymmetric synthesis of chiral cycloalkenone derivatives via palladium catalysis
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3992253/
https://www.ncbi.nlm.nih.gov/pubmed/24761221
http://dx.doi.org/10.1039/c3sc53250j
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