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Direct Trapping of Sterically Encumbered Aluminum Enolates

Published in Organic Letters. 2013, vol. 15, no. 9, p. 2152-2155
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.
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Other version: http://pubs.acs.org/doi/abs/10.1021/ol400642y
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BLESCHKE, Christian Alexander et al. Direct Trapping of Sterically Encumbered Aluminum Enolates. In: Organic Letters, 2013, vol. 15, n° 9, p. 2152-2155. https://archive-ouverte.unige.ch/unige:27733

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Deposited on : 2013-05-08

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