A [Cu((S,S)-t-Bu-box)](X)2 complex activates �-amidoaldehydes to allow stereospecific nucleophilic substitution at the aldehyde.  The catalyst is effective for the stereospecific addition of chiral amidoaldehydes to activated oxazoles because it is a divalent Lewis acid, serving to constrain the conformation of the bidentate amidoaldehyde and to activate the aldehyde toward nucleophilic addition.  Activation of chiral �-amidoaldehydes has previously been demonstrated with a dialkylaluminum catalyst that resulted in the desired nucleophilic addition, as well as the alkylation of the aldehyde by the alkyl groups of the catalyst.  Applications of this chemistry include the synthesis of complex amino acid related natural products.  The optimization and variations of the copper catalyst, as well as variations of the aldehyde, will be discussed.

Stereospecific electrophilic addition of amidoaldehydes to oxazoles using Lewis acid catalysts

243rd National Meeting (2012)

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