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 אוג 2021
Accepted
27 ספט 2021
First published
27 ספט 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements