Abstract
The high levels of 1,2-stereocontrol observed in nucleophilic additions to ( S)-2-(dibenzylamino)-3-phenylpropanal (available in three high-yielding steps from l-phenylalanine) can be converted to remote 1,4-stereocontrol by a stereospecific rearrangement if the nucleophile is a vinyl anion equivalent. Ozonolysis of the product followed by reductive work-up returns an enantiomerically pure 2-substituted alcohol, along with the ( S)-2-(dibenzylamino)-3-phenylpropan-1-ol precursor to the starting aldehyde, which functions as a chiral auxiliary. The sequence provides a new strategy for the use of aldehydes as chiral auxiliaries in the synthesis of chiral alcohols bearing oxygen- or carbon-based 2-substituents.
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