Stereoselective Synthesis of Highly Substituted 1,3-Dienes via “à la carte” Multifunctionalization of Borylated Dendralenes
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Título: | Stereoselective Synthesis of Highly Substituted 1,3-Dienes via “à la carte” Multifunctionalization of Borylated Dendralenes
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Autor/a: | Rivera Chao, Eva
Fañanás Mastral, Martín
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Centro/Departamento: | Universidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares Universidade de Santiago de Compostela. Departamento de Química Orgánica
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Palabras chave: | 1,3-dienes | Boron | Carbolithiation | Dendralenes | Multicomponent reactions | |
Data: | 2021
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Editor: | Wiley
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Cita bibliográfica: | E. Rivera-Chao, M. Fañanás-Mastral, Angew. Chem. Int. Ed. 2021, 60, 16922.
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Resumo: | Despite the high relevance of 1,3-dienes, stereoselective methods to access tetrasubstituted conjugated dienes are still scarce. We here report an efficient and modular approach that provides access to multifunctional tetrasubstituted 1,3-dienes with excellent levels of regio- and stereoselectivity. This methodology is based on a tetracomponent reaction between a borylated dendralene, an organolithium reagent and two different electrophiles. Mechanistic studies reveal that this transformation proceeds through a regio- and stereoselective carbolithiation/electrophilic trapping of an in situ formed dendralenic boron-ate complex, followed by a stereoretentive halodeborylation. The ease in which complex structural dienes can be accessed and their synthetic versatility highlight the importance and utility of this method |
Versión do editor: | https://doi.org/10.1002/anie.202104741 |
URI: | http://hdl.handle.net/10347/26627
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DOI: | 10.1002/anie.202104741 |
ISSN: | 1433-7851
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E-ISSN: | 1521-3773
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Dereitos: | © 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made Attribution-NonCommercial-NoDerivatives 4.0 Internacional
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