316. C. Bleschke, M. Tissot, D. Müller, A. Alexakis,
     “Direct Trapping of Sterically Encumbered Aluminum Enolates”
     Org. Lett. 2013, 15, 2152-2155.

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.

DOI : 10.1021/ol400642y 

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