Stereodivergent Silylzincation of α-Heteroatom-Substituted Alkynes
| Autor: | Elise Romain, Alejandro Perez-Luna, Franck Ferreira, Carolin Fopp, Fabrice Chemla, Olivier Jackowski, Kévin Isaac, Martin Oestreich |
|---|---|
| Přispěvatelé: | Institut für Chemie [TUB Berlin], Technical University of Berlin / Technische Universität Berlin (TU), Institut Parisien de Chimie Moléculaire (IPCM), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Réactivité organométallique et catalyse pour la synthèse (ROCS), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Technische Universität Berlin (TU), Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS) |
| Jazyk: | angličtina |
| Rok vydání: | 2016 |
| Předmět: |
chemistry.chemical_classification
Double bond Silylation 010405 organic chemistry Stereochemistry Organic Chemistry Heteroatom chemistry.chemical_element 010402 general chemistry Triple bond 01 natural sciences Biochemistry Copper 0104 chemical sciences Catalysis Electrophilic substitution chemistry [CHIM]Chemical Sciences Stereoselectivity Physical and Theoretical Chemistry ComputingMilieux_MISCELLANEOUS |
| Zdroj: | Organic Letters Organic Letters, 2016, 18 (9), pp.2054--2057. ⟨10.1021/acs.orglett.6b00680⟩ Organic Letters, American Chemical Society, 2016, 18 (9), pp.2054--2057. ⟨10.1021/acs.orglett.6b00680⟩ |
| ISSN: | 1523-7060 1523-7052 |
| Popis: | Zinc reagents (Me2PhSi)2Zn and [(Me3Si)3Si]2Zn undergo highly regio- and stereoselective addition across the carbon-carbon triple bond of nitrogen-, sulfur-, oxygen-, and phosphorus-substituted terminal alkynes in the absence of copper or any other catalyst. Both reagents yield exclusively β-isomers, and the stereoselectivity is determined by the silyl group: Me2PhSi for cis or (Me3Si)3Si for trans. These stereodivergent silylzincation protocols offer an efficient access to heteroatom-substituted vinylsilanes with either double bond geometry, including trisubstituted vinylsilanes by one-pot electrophilic substitution of the intermediate C(sp(2))-Zn bond by copper(I)-mediated carbon-carbon bond formation. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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