TY - JOUR
T1 - Highly enantioselective electrophilic amination and Michael addition of cyclic β-ketoesters induced by lanthanides and (S,S)-ip-pybox: The mechanism
AU - Comelles, Josep
AU - Pericas, Alex
AU - Moreno-Mañas, Marcial
AU - Vallribera, Adelina
AU - Drudis-Solé, Galí
AU - Lledos, Agusti
AU - Parella, Teodor
AU - Roglans, Anna
AU - García-Granda, Santiago
AU - Roces-Fernández, Laura
PY - 2007/3/16
Y1 - 2007/3/16
N2 - High enantioselection is obtained in Michael additions of cyclic β-ketoesters in the presence of lanthanium triflates and (S,S)-ip-pybox. Intermediates based on simultaneous coordination of the lanthanide to both (S,S)-ip-box and β-ketoester (in keto and enolate forms) are detected by means of ESI mass spectrometry and NMR experiments, and a possible mechanism is proposed through theoretical calculations. © 2007 American Chemical Society.
AB - High enantioselection is obtained in Michael additions of cyclic β-ketoesters in the presence of lanthanium triflates and (S,S)-ip-pybox. Intermediates based on simultaneous coordination of the lanthanide to both (S,S)-ip-box and β-ketoester (in keto and enolate forms) are detected by means of ESI mass spectrometry and NMR experiments, and a possible mechanism is proposed through theoretical calculations. © 2007 American Chemical Society.
U2 - 10.1021/jo0622678
DO - 10.1021/jo0622678
M3 - Article
SN - 0022-3263
VL - 72
SP - 2077
EP - 2087
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 6
ER -