Issue 80, 2015

Organocatalytic dynamic kinetic resolution of azlactones to construct chiral N-acyl amino acid oxime esters

Abstract

A direct strategy to obtain N-acyl amino acid oxime esters has been developed through the dynamic kinetic resolution of azlactones with oximes. In the presence of a chiral bisguanidinium salt catalyst, a variety of chiral N-acyl amino acid oxime esters were generated in excellent enantiomeric excesses (up to 97%) and high yields (up to 99%). The active oxime esters could be used in dipeptide synthesis.

Graphical abstract: Organocatalytic dynamic kinetic resolution of azlactones to construct chiral N-acyl amino acid oxime esters

Supplementary files

Article information

Article type
Communication
Submitted
05 Jul 2015
Accepted
18 Aug 2015
First published
25 Aug 2015

Chem. Commun., 2015,51, 14897-14900

Organocatalytic dynamic kinetic resolution of azlactones to construct chiral N-acyl amino acid oxime esters

K. Yu, X. Liu, X. Lin, L. Lin and X. Feng, Chem. Commun., 2015, 51, 14897 DOI: 10.1039/C5CC05534B

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