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
Journal	Angewandte Chemie International Edition
DOIs	https://doi.org/10.1002/anie.202217178
Publication status	Accepted/In press - 30 Jan 2023

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10.1002/anie.202217178

Sulfonamide RE paper ACIE version 6 REVISIONAccepted author manuscript, 2.28 MB

Cite this

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title = "Ring Expansion Strategies for the Synthesis of Medium Sized Ring and Macrocyclic Sulfonamides",

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.",

author = "Zhongzhen Yang and Illya Zalessky and Epton, {Ryan G} and Whitwood, {Adrian C} and Lynam, {Jason M} and Unsworth, {William Paul}",

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AU - Yang, Zhongzhen

AU - Zalessky, Illya

AU - Epton, Ryan G

AU - Whitwood, Adrian C

AU - Lynam, Jason M

AU - Unsworth, William Paul

PY - 2023/1/30

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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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DO - 10.1002/anie.202217178

M3 - Article

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