Bridge functionalisation of bicyclo[1.1.1]pentane derivatives

Anderson, Joseph M. and Measom, Nicholas D. and Murphy, John A. and Poole, Darren L. (2021) Bridge functionalisation of bicyclo[1.1.1]pentane derivatives. Angewandte Chemie International Edition, 60 (47). pp. 24754-24769. ISSN 1521-3773 (https://doi.org/10.1002/anie.202106352)

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Abstract

"Escaping from flatland", by increasing the saturation level and three-dimensionality of drug-like compounds, can enhance their potency, selectivity and pharmacokinetic profile. One approach that has attracted considerable recent attention is the bioisosteric replacement of aromatic rings, internal alkynes and tert-butyl groups with bicyclo[1.1.1]pentane (BCP) units. While functionalisation of the tertiary bridgehead positions of BCP derivatives is well-documented, functionalisation of the three concyclic secondary bridge positions remains an emerging field. The unique properties of the BCP core present considerable synthetic challenges to the development of such transformations. However, the bridge positions provide novel vectors for drug discovery and applications in materials science, providing entry to novel chemical and intellectual property space. This minireview aims to consolidate the major advances in the field, serving as a useful reference to guide further work that is expected in the coming years.

ORCID iDs

Anderson, Joseph M., Measom, Nicholas D. ORCID logoORCID: https://orcid.org/0000-0001-5627-0366, Murphy, John A. and Poole, Darren L.;
  • Item type:Article
    ID code:77846
    Dates:
    Date
    Event
    15 November 2021
    Published
    20 June 2021
    Published Online
    18 June 2021
    Accepted
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:21 Sep 2021 15:06
    Last modified:24 Nov 2024 01:22
    URI:https://strathprints.strath.ac.uk/id/eprint/77846
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