Synthesis 2016; 48(13): 2036-2049
DOI: 10.1055/s-0035-1561943
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© Georg Thieme Verlag Stuttgart · New York

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
› Author Affiliations
Further Information

Publication History

Received: 01 February 2016

Accepted: 19 February 2016

Publication Date:
26 April 2016 (eFirst)

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.

 
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