Issue 64, 2020

Design, synthesis and characterization of structurally dynamic cyclic N,S-acetals

Abstract

We report the synthesis, characterization and comparison of a series of electronically perturbed, cyclic N,S-acetals. Inspired by electrophilic auxiliaries utilized for amine capture and concomitant peptide ligation, we studied these N,S-acetal systems and evaluated their propensity to generate zwitterionic intermediates in situ. Certain N,S-acetals in this study exhibit structurally dynamic properties through a solvent and pH-dependent ability to ring-open and ring-close via C1–S bond ionization at room temperature.

Graphical abstract: Design, synthesis and characterization of structurally dynamic cyclic N,S-acetals

Supplementary files

Article information

Article type
Communication
Submitted
16 Mei 2020
Accepted
06 Jul 2020
First published
07 Jul 2020

Chem. Commun., 2020,56, 9118-9121

Design, synthesis and characterization of structurally dynamic cyclic N,S-acetals

E. K. Kirkeby and A. G. Roberts, Chem. Commun., 2020, 56, 9118 DOI: 10.1039/D0CC03503C

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