Enantiospecific Synthesis of 1,3-Disubstituted Allenes from Propargylic Carbonates through a Borylation-1,2-Elimination Process

An array of enantioenriched vinyl boronates bearing an allylic carbonate moiety have been prepared through selective hydroboration of propargyl carbonates. Treatment of these vinyl boronates with TBAF in THF affords enantioenriched 1,3-disubstituted allenes through a novel 1,2-anti elimination in go...

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Detalles Bibliográficos
Autores: Jarava-Barrera, Carlos, Parra, Alejandro, Quesada, Sergio, Orgaz-Gordillo, Sergio, Fernández de la Pradilla, Roberto, Viso, Alma, Teresa, Javier, Alonso, Inés, Tortosa, Mariola
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2024
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/395544
Acceso en línea:http://hdl.handle.net/10261/395544
https://api.elsevier.com/content/abstract/scopus_id/85177649840
Access Level:acceso abierto
Palabra clave:1,2-anti-elimination
Allenes
Boronates
Propargylic carbonates
TBAF
Descripción
Sumario:An array of enantioenriched vinyl boronates bearing an allylic carbonate moiety have been prepared through selective hydroboration of propargyl carbonates. Treatment of these vinyl boronates with TBAF in THF affords enantioenriched 1,3-disubstituted allenes through a novel 1,2-anti elimination in good yields and high enantiospecificities.