Issue 84, 2021

Stereodivergent silver-catalyzed synthesis of pyroglutamic acid esters

Abstract

We report here a silver-catalyzed method for the enantio- and diastereodivergent synthesis of chiral pyroglutamic acid esters with multiple stereocenters. This process proceeds through asymmetric conjugate addition of glycine imine esters to a broad range of β-substituted α,β-unsaturated perfluorophenyl esters followed by lactamization. By leveraging catalyst control and stereospecificity of the 1,4-addition process, all four product stereoisomers containing two adjacent stereocenters are accessible with high stereoselectivity.

Graphical abstract: Stereodivergent silver-catalyzed synthesis of pyroglutamic acid esters

Supplementary files

Article information

Article type
Communication
Submitted
31 août 2021
Accepted
27 sept. 2021
First published
27 sept. 2021

Chem. Commun., 2021,57, 11052-11055

Stereodivergent silver-catalyzed synthesis of pyroglutamic acid esters

B. Kim, Y. Song and S. Y. Lee, Chem. Commun., 2021, 57, 11052 DOI: 10.1039/D1CC04875A

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