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Artigo Produção Nacional Revisado por pares
BIBTEX RIS

Probing the mechanism of direct Mannich‐type α‐methylenation of ketoesters via electrospray ionization mass spectrometry

2007; Wiley; Volume: 42; Issue: 10 Linguagem: Inglês

10.1002/jms.1173

ISSN

1096-9888

Autores

Cíntia D. F. Milagre, Humberto M. S. Milagre, Leonardo S. Santos, Marcelo L. A. Lopes, Paulo J. S. Moran, Marcos N. Eberlin, J. Augusto R. Rodrigues,

Tópico(s)

Asymmetric Synthesis and Catalysis

Resumo

Reactions promoting direct Mannich-type alpha-methylenation of alpha, beta and gamma-ketoesters have been monitored via electrospray ionization mass and tandem mass spectrometric experiments. Key intermediates of the catalytical cycle of this synthetically useful reaction have been intercepted and characterized. The mechanistic information provided by electrospray ionization mass spectrometry/mass spectrometry (ESI-MS/MS) guided the optimization of reaction conditions, allowing alpha-methyleneketoesters to be prepared in high yields (80-95%) and in high-enough purity for immediate further manipulation.

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