Issue 30, 2023

2,5-disubstituted bicyclo[2.1.1]hexanes as rigidified cyclopentane variants

Abstract

Identification of rigid counterparts for common flexible scaffolds is crucial to the advancement of medicinal chemistry. Here we showcase a new class of building blocks, 2,5-disubstituted bicyclo[2.1.1]hexanes that can act as rigidified cis-, or trans-1,3-disubstituted cyclopentanes, common motifs in drugs. The scalable synthesis of these structures was enabled through the use of C–H functionalization logic and cycloaddition reactions.

Graphical abstract: 2,5-disubstituted bicyclo[2.1.1]hexanes as rigidified cyclopentane variants

Supplementary files

Article information

Article type
Edge Article
Submitted
27 mei 2023
Accepted
06 jul 2023
First published
12 jul 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2023,14, 8070-8075

2,5-disubstituted bicyclo[2.1.1]hexanes as rigidified cyclopentane variants

S. Paul, D. Adelfinsky, C. Salome, T. Fessard and M. K. Brown, Chem. Sci., 2023, 14, 8070 DOI: 10.1039/D3SC02695G

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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