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Utilice este identificador para citar o enlazar este documento: https://ria.asturias.es/RIA/handle/123456789/13026


Título: Domino Synthesis of Benzo-fused β,γ-Unsaturated Ketones from Alkenylboronic acids and N-Tosylhydrazone-tethered Benzonitriles
Autores: Florentino Rico, Lucía
Valdés Gómez, Alfonso Carlos
Plaza, Manuel
Paraja, Miguel
Palabras Claves: Organic Chemistry
Transition-metal-free
Domino reaction
Stereoselective
Fecha Edición: 14-Ene-2019
Editor: American Chemical Society
Cita Bibliográfica: Plaza, M.; Paraja, M; Florentino, L.; Valdés, C. Org. Lett., 2019, 21 (3), 632.
Resumen: The transition-metal-free domino reaction between alkenylboronic acids and N-tosylhydrazones from o-(2-oxoalkyl)- and o-(3-oxoalkyl)benzonitriles leads to β,γ-unsaturated indanones and tetralones featuring an α-“all-carbon” quaternary center. The employment of derivatives of α-substituted cyclopentanones and cyclohexanones led to the stereoselective preparation of β,γ-unsaturated tetrahydrocyclopenta[a]inden-8(1H)-ones, hexahydrofluorenones, and hexahydroanthracenones as cis-fused single stereoisomers. A domino sequence involving diazo compound formation/reductive alkenylation/1,3-borotropic rearrangement/intramolecular bora-aza-ene reaction is proposed to justify the formation of the products as well as the stereoselectivity.
URI: https://ria.asturias.es/RIA/handle/123456789/13026
ISSN: 1523-7060
Aparece en las Colecciones:Química
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