Asymmetric Nucleophilic a-Aminoacylation

Asymmetric Syntheses with Lithiated a-Aminonitriles 1.1.4.1 Asymmetric Nucleophilic a-Aminoacylation 

C synthons, synthetic equivalents of which being the amino-acetaldehyde-derived metallated aminonitrile D bearing the chiral auxiliary (S,S)-53 and an a,P-unsaturated ester E, respectively. This should make it possible to open up a pathway to an enantioselective conjugate addition of an a-aminoacyl carbanion equivalent D to enoates in order to access the target 3-substituted 5-ainino-4-oxo esters. 

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Scheme 1.1.14 Retrosynthetic strategy for the asymmetric nucleophilic a-aminoacylation.

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