Probing the mechanism of direct Mannich-type alpha-methylenation of ketoesters via electrospray ionization mass spectrometry.
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.
Milagre
Cíntia D F
CD
Institute of Chemistry, State University of Campinas, 13084-971 Campinas, SP, Brazil.
Milagre
Humberto M S
HM
Santos
Leonardo S
LS
Lopes
Marcelo L A
ML
Moran
Paulo J S
PJ
Eberlin
Marcos N
MN
Rodrigues
J Augusto R
JA