title: Direct trapping of sterically encumbered aluminum enolates.
abstract: The formation of chiral and sterically congested cyclohexanone derivatives has been achieved through a multistep sequence with one single purification step. (n-Butoxymethyl)-diethylamine was identified as a highly efficient reagent for the direct trapping of aluminum enolates. The Lewis acidic character of aluminum suffices to activate the α-aminoether to form in situ an electrophilic iminium species. In return the aluminum enolate is rendered more nucleophilic by coordination of the butoxy group and formation of an aluminate.
authors.affiliation: Department of Organic Chemistry, University of Geneva, Quai Ernest Ansermet 30, CH-1211 Geneva 4, Switzerland.
authors.forename: Christian
authors.initials: C
authors.lastname: Bleschke
authors.forename: Matthieu
authors.initials: M
authors.lastname: Tissot
authors.forename: Daniel
authors.initials: D
authors.lastname: Müller
authors.forename: Alexandre
authors.initials: A
authors.lastname: Alexakis