Issue 38, 2024

Cascade ring expansion reactions for the synthesis of medium-sized rings and macrocycles

Abstract

This Feature Article discusses recent advances in the development of cascade ring expansion reactions for the synthesis of medium-sized rings and macrocycles. Cascade ring expansion reactions have much potential for use in the synthesis of biologically important medium-sized rings and macrocycles, most notably as they don’t require high dilution conditions, which are commonly used in established end-to-end macrocyclisation methods. Operation by cascade ring expansion method can allow large ring products to be accessed via rearrangements that proceed exclusively by normal-sized ring cyclisation steps. Ensuring that there is adequate thermodynamic driving force for ring expansion is a key challenge when designing such methods, especially for the expansion of normal-sized rings into medium-sized rings. This Article is predominantly focused on methods developed in our own laboratory, with selected works by other groups also discussed. Thermodynamic considerations, mechanism, reaction design, route planning and future perspective for this field are all covered.

Graphical abstract: Cascade ring expansion reactions for the synthesis of medium-sized rings and macrocycles

Article information

Article type
Feature Article
Submitted
21 mar 2024
Accepted
16 apr 2024
First published
18 apr 2024
This article is Open Access
Creative Commons BY-NC license

Chem. Commun., 2024,60, 4999-5009

Cascade ring expansion reactions for the synthesis of medium-sized rings and macrocycles

J. M. Wootton, J. K. F. Tam and W. P. Unsworth, Chem. Commun., 2024, 60, 4999 DOI: 10.1039/D4CC01303D

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