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Related Experiment Video

Updated: May 14, 2025

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

A Sydnonimine-based Click-and-Release Approach to Cyclic Products.

Guillaume Force¹, Minghao Feng¹, Davide Audisio¹

¹CEA, INRAE, Département Médicaments et Technologies pour la Santé (DMTS), SCBM, Université Paris Saclay, Gif-sur-Yvette, 91191, France.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|April 11, 2025

Summary

A new method efficiently creates cyclic compounds using copper-catalyzed click-and-release reactions and a hydrophobic tag. This practical approach yields diverse cyclic products without requiring purification.

Keywords:

click‐and‐release copper cycloaddition macrocycles sydnonimines

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Last Updated: May 14, 2025

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Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

Macrocyclization is crucial for synthesizing complex molecules.
Existing methods often require extensive purification or lack versatility.

Purpose of the Study:

To develop a general, efficient, and practical methodology for macrocyclization.
To enable the synthesis of diverse cyclic compounds without purification.

Main Methods:

Utilized a copper-catalyzed click-and-release reaction.
Incorporated a hydrophobic tag to facilitate macrocyclization.
Developed a one-pot procedure.

Main Results:

Successfully synthesized cyclic products of various sizes and functionalities.
Demonstrated the efficiency and practicality of the methodology.
Eliminated the need for intermediate purification steps.

Conclusions:

The reported methodology provides a robust platform for macrocyclization.
This approach simplifies the synthesis of cyclic molecules, enhancing accessibility.
The click-and-release strategy offers a versatile tool for organic synthesis.