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Probing the mechanism of direct Mannich‐type α‐methylenation of ketoesters via electrospray ionization mass spectrometry
Author(s) -
Milagre Cíntia D. F.,
Milagre Humberto M. S.,
Santos Leonardo S.,
Lopes Marcelo L. A.,
Moran Paulo J. S.,
Eberlin Marcos N.,
Rodrigues J. Augusto R.
Publication year - 2007
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/jms.1173
Subject(s) - chemistry , electrospray ionization , mass spectrometry , tandem mass spectrometry , extractive electrospray ionization , electrospray , mannich reaction , chromatography , electrospray mass spectrometry , combinatorial chemistry , protein mass spectrometry , organic chemistry , catalysis
Abstract Reactions promoting direct Mannich‐type α‐methylenation of α, β and γ‐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 α‐methyleneketoesters to be prepared in high yields (80–95%) and in high‐enough purity for immediate further manipulation. Copyright © 2007 John Wiley & Sons, Ltd.