Desymmetrization of C2-Symmetric Bis(Boronic Esters) by Zweifel Olefinations

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Linne, Y.; Schönwald, A.; Weißbach, S.; Kalesse, M.: Desymmetrization of C2-Symmetric Bis(Boronic Esters) by Zweifel Olefinations. In: Chemistry - A European Journal 26 (2020), Nr. 36, S. 7998-8002. DOI: https://doi.org/10.1002/chem.202000599

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Sum total of downloads: 219




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Abstract: 
anti-Configured 1,3-dimethyl deoxypropionate motifs are important sub structures in natural products. Herein, we describe a bidirectional approach for the rapid construction of natural products featuring such motifs by using C2-symmetrical 1,3-bis(boronic esters). As for its application in convergent syntheses it was important to establish a selective mono-Zweifel olefination we describe the scope and limitations by using different 1,3-bis(boronic esters) and nucleophiles. This protocol takes advantage of the combination of the Hoppe–Matteson–Zweifel chemistry, which was elegantly put into practice by Aggarwal et al. In order to show its applicability the total syntheses of two natural products, serricornin and (+)-invictolide, were performed. © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
License of this version: CC BY 4.0 Unported
Document Type: Article
Publishing status: publishedVersion
Issue Date: 2020
Appears in Collections:Naturwissenschaftliche Fakultät

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pos. country downloads
total perc.
1 image of flag of Germany Germany 148 67.58%
2 image of flag of United States United States 32 14.61%
3 image of flag of China China 8 3.65%
4 image of flag of No geo information available No geo information available 4 1.83%
5 image of flag of United Kingdom United Kingdom 4 1.83%
6 image of flag of Russian Federation Russian Federation 3 1.37%
7 image of flag of Israel Israel 2 0.91%
8 image of flag of France France 2 0.91%
9 image of flag of Czech Republic Czech Republic 2 0.91%
10 image of flag of Switzerland Switzerland 2 0.91%
    other countries 12 5.48%

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