While stereoselective addition of aldehydes to activated oxazoles using chiral catalysts has been previously described in detail, reactions which use chirality within the aldehyde to generate high diastereoselectivity are much less common.  We have studied a variety of Lewis acids as catalysts for the addition of chiral amidoaldehydes to activated aryl oxazoles.  Catalysts which allow the amidoaldehyde to serve as a bidentate ligand, thereby enforcing conformational rigidity of the aldehyde, have resulted in complete diastereoselectivity under appropriate conditions.  The reaction results in rearranged oxazoline product.  The effectiveness of specific Lewis acids, the conditions required for effective complexation, and applications of this chemistry to the synthesis of complex amino acid related natural products will be discussed.

Diastereoselective addition of chiral amidoaldehydes to aryl substituted oxazoles

239th National Meeting (2010)

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