Synthesis of axially chiral heterobiaryl alkynes via dynamic kinetic asymmetric alkynylation

The dynamic kinetic Pd0-catalyzed alkynylation of racemic heterobiaryl sulfonates was used for the asymmetric synthesis of axially chiral heterobiaryl alkynes with a broad scope. The use of Pd(OAc)2/(S)-QUINAP as the precatalyst provides products in excellent yields and enantioselectivities under mi...

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Detalhes bibliográficos
Autores: Hornillos, Valentín, Ros, Abel, Ramírez-López, Pedro, Iglesias-Sigüenza, Javier, Fernández, Rosario, Lassaletta, José M.
Tipo de documento: artigo
Estado:Versão publicada
Data de publicação:2016
País:España
Recursos:Consejo Superior de Investigaciones Científicas (CSIC)
Repositório:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/141903
Acesso em linha:http://hdl.handle.net/10261/141903
Access Level:Acceso aberto
Descrição
Resumo:The dynamic kinetic Pd0-catalyzed alkynylation of racemic heterobiaryl sulfonates was used for the asymmetric synthesis of axially chiral heterobiaryl alkynes with a broad scope. The use of Pd(OAc)2/(S)-QUINAP as the precatalyst provides products in excellent yields and enantioselectivities under mild conditions (DMSO, 40 °C). Semireduction, 1,3-dipolar cycladdition or N-oxidation served to illustrate the synthetic potential of the methodology.