Synthesis of an Alkylidene 2-Oxazolidinone via Gold-Catalyzed Cyclization of a N-Boc-Allenylaniline

Abstract

N-Boc-allenylaniline undergoes cyclization in the presence of a catalytic amount of a cationic gold complex to exclusively form 2-oxazolidinones, whereas the N-Moc-allenylaniline affords dihydroquinolines.

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GRAPHICAL ABSTRACT

Keywords:

• Allenes
• catalyst
• dihydroquinolines
• gold
• hydroarylation
• 2-oxazolidinones

ACKNOWLEDGMENTS

The authors thank the Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq), the Fundação Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES), and the Fundação de Amparo à Pesquisa do Estado de Minas Gerais (FAPEMIG) for financial support. Thanks go to Dr. Robson J. de Cássia FrancoAfonso, and Dr. Maurício Xavier Coutrim for providing excellent Mass Spectrometry service.