Stereospecific Meisenheimer rearrangement

The natural product (R)-sulcatol is a male-produced aggregation pheromone of the ambrosia beetle. This insect can devastate entire forests when its population is out of control.Various studies revealed that different species respond to the compound in different enantiomeric excess. The asymmetric synthesis of (R)-sulcatol was accomplished in the laboratory of S.G. Davies using a stereospecific [2,3]-Meisenheimer rearrangement as the key step. The treatment of the allylic amine substrate with mCPBA followed by the filtration of the reaction mixture through deactivated basic alumina afforded the desired hydroxylamine as a single diastereomer. 

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