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

Marc Hutchby; Adam C. Sedgwick; Steven D. Bull

doi:10.1055/s-0035-1561943

Synthesis, Inhaltsverzeichnis

Synthesis 2016; 48(13): 2036-2049
DOI: 10.1055/s-0035-1561943

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

Marc Hutchby

Department of Chemistry, University of Bath, Bath BA2 7AY, UK eMail: s.d.bull@bath.ac.uk

,

Adam C. Sedgwick

Department of Chemistry, University of Bath, Bath BA2 7AY, UK eMail: s.d.bull@bath.ac.uk

,

Steven D. Bull*

Department of Chemistry, University of Bath, Bath BA2 7AY, UK eMail: s.d.bull@bath.ac.uk

› Institutsangaben

Abstract

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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

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Referenzen

References

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