Use chiral bases that can promote the rearrangement while providing chirality to the reaction. One common example is using a chiral phosphine as a base. The phosphine can deprotonate the carboxamide to initiate the rearrangement while transferring chirality from the phosphine to the product. Ligands like (R)-BINAP or (R)-SEGPHOS can be used in this context.
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N-((S)-1-phenylethyl)-(2S,3S)-2,3-dimethylpent-4-enamide
(S,S)-(-)-2,3-DIHYDROXY-N,N,N',N'-TETRAMETHYLSUCCINAMIDE
