Ring Expansion Strategies for the Synthesis of Medium Sized Ring and Macrocyclic Sulfonamides

Zhongzhen Yang; Illya Zalessky; Ryan G Epton; Adrian C Whitwood; Jason M Lynam; William Paul Unsworth

doi:10.1002/anie.202217178

Ring Expansion Strategies for the Synthesis of Medium Sized Ring and Macrocyclic Sulfonamides

Zhongzhen Yang, Illya Zalessky, Ryan G Epton, Adrian C Whitwood, Jason M Lynam, William Paul Unsworth

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

Two new ring expansion strategies are reported for the synthesis of medium sized ring and macrocyclic sulfonamides. Both methods can be performed without using classical protecting groups, with the key ring expansion step initiated by nitro reduction and amine conjugate addition respectively. Each method can be used to make diversely functionalised cyclic sulfonamides in good to excellent yields, in a range of ring sizes. The ring size dependency of the synthetic reactions is in good agreement with the outcomes modelled by Density Functional Theory calculations.

Original language	English
Article number	e202217178
Number of pages	6
Journal	Angewandte Chemie International Edition
Volume	62
Early online date	15 Feb 2023
DOIs	https://doi.org/10.1002/anie.202217178
Publication status	Published - 20 Mar 2023

Bibliographical note

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10.1002/anie.202217178Licence: CC BY

Angew Chem Int Ed - 2023 - Yang - Ring Expansion Strategies for the Synthesis of Medium Sized Ring and Macrocyclic
© 2023 The Authors.
Final published version, 5.1 MBLicence: CC BY

Cite this

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abstract = "Two new ring expansion strategies are reported for the synthesis of medium sized ring and macrocyclic sulfonamides. Both methods can be performed without using classical protecting groups, with the key ring expansion step initiated by nitro reduction and amine conjugate addition respectively. Each method can be used to make diversely functionalised cyclic sulfonamides in good to excellent yields, in a range of ring sizes. The ring size dependency of the synthetic reactions is in good agreement with the outcomes modelled by Density Functional Theory calculations.",

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AU - Zalessky, Illya

AU - Epton, Ryan G

AU - Whitwood, Adrian C

AU - Lynam, Jason M

AU - Unsworth, William Paul

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N2 - Two new ring expansion strategies are reported for the synthesis of medium sized ring and macrocyclic sulfonamides. Both methods can be performed without using classical protecting groups, with the key ring expansion step initiated by nitro reduction and amine conjugate addition respectively. Each method can be used to make diversely functionalised cyclic sulfonamides in good to excellent yields, in a range of ring sizes. The ring size dependency of the synthetic reactions is in good agreement with the outcomes modelled by Density Functional Theory calculations.

AB - Two new ring expansion strategies are reported for the synthesis of medium sized ring and macrocyclic sulfonamides. Both methods can be performed without using classical protecting groups, with the key ring expansion step initiated by nitro reduction and amine conjugate addition respectively. Each method can be used to make diversely functionalised cyclic sulfonamides in good to excellent yields, in a range of ring sizes. The ring size dependency of the synthetic reactions is in good agreement with the outcomes modelled by Density Functional Theory calculations.

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