Highly Enantioselective Electrophilic Amination and Michael Addition of Cyclic β-Ketoesters Induced by Lanthanides and (S,S)-ip-pybox: The Mechanism
The Journal of Organic Chemistry2007Vol. 72(6), pp. 2077–2087
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Josep M. Comelles, Àlex Pericas, Marcial Moreno‐Mañas, Adelina Vallribera, Galí Drudis‐Solé, Agustı́ Lledós, Teodor Parella, Anna Roglans, Santiago Garcı́a-Granda, L. Roces-Fernandez
Abstract
High enantioselection is obtained in Michael additions of cyclic beta-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 beta-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.
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