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Issue 64, 2020
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Design, synthesis and characterization of structurally dynamic cyclic N,S-acetals

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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

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Submitted
16 May 2020
Accepted
06 Jul 2020
First published
07 Jul 2020

Chem. Commun., 2020,56, 9118-9121
Article type
Communication

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

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