Electrophilic Rearrangements of Chiral Amides: A Traceless Asymmetric α-Allylation
Journal of the American Chemical Society2013Vol. 135(40), pp. 14968–14971
Citations Over TimeTop 10% of 2013 papers
Abstract
A one-pot protocol for the asymmetric α-allylation reaction is reported relying on a key efficient asymmetric Claisen rearrangement, triggered by electrophilic activation of chiral pseudoephedrine amides. Subsequent reduction or hydrolysis of the resulting iminium ions provides highly enantioenriched α-allylic aldehydes or carboxylic acids in a traceless manner. Compared to traditional alternatives which make use of strongly basic conditions, the work presented herein displays unprecedented functional group tolerance.
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