Orthogonally Protected Schöllkopf’s Bis-lactim Ethers for the Asymmetric Synthesis of α-Amino Acid Derivatives and Dipeptide Esters

Abstract

Alkylation of the aza-enolates of orthogonally protected chiral bis-lactim ethers with electrophiles proceeds with good levels of diastereocontrol to afford trans-alkylated adducts that can be efficiently deprotected via hydrolysis/hydrogenation procedures to afford non-proteinogenic α-amino acid or dipeptide ester derivatives.

Key words

asymmetric synthesis - orthogonal protection - bis-lactim ethers - hydrogenolysis - separation - non-proteinogenic - chiral α-amino acids - dipeptide esters

• References

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