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

Research output: Contribution to journal › Article

7 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)2036-2049
JournalSynthesis
Volume48
Issue number13
Early online date26 Apr 2016
DOIs
Publication statusPublished - Jul 2016

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Ethers
Dipeptides
Alkylation
Hydrogenation
Amino acids
Hydrolysis
Esters
Derivatives
Amino Acids

Cite this

Orthogonally protected Schöllkopf’s bis-lactim ethers for the asymmetric synthesis of α-amino acid derivatives and dipeptide esters. / Hutchby, Marc; Sedgwick, Adam C; Bull, Steven D.

In: Synthesis, Vol. 48, No. 13, 07.2016, p. 2036-2049.

Research output: Contribution to journal › Article

Hutchby, M, Sedgwick, AC & Bull, SD 2016, 'Orthogonally protected Schöllkopf’s bis-lactim ethers for the asymmetric synthesis of α-amino acid derivatives and dipeptide esters', Synthesis, vol. 48, no. 13, pp. 2036-2049. https://doi.org/10.1055/s-0035-1561943
Hutchby M, Sedgwick AC, Bull SD. Orthogonally protected Schöllkopf’s bis-lactim ethers for the asymmetric synthesis of α-amino acid derivatives and dipeptide esters. Synthesis. 2016 Jul;48(13):2036-2049. https://doi.org/10.1055/s-0035-1561943
Hutchby, Marc ; Sedgwick, Adam C ; Bull, Steven D. / Orthogonally protected Schöllkopf’s bis-lactim ethers for the asymmetric synthesis of α-amino acid derivatives and dipeptide esters. In: Synthesis. 2016 ; Vol. 48, No. 13. pp. 2036-2049.
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