Journal article : Review

Conquering the synthesis and functionalization of bicyclo[1.1.1]pentanes

Abstract:: Bicyclo[1.1.1]pentanes (BCPs) have become established as attractive bioisosteres for para-substituted benzene rings in drug design. Conferring various beneficial properties compared with their aromatic “parents,” BCPs featuring a wide array of bridgehead substituents can now be accessed by an equivalent variety of methods. In this perspective, we discuss the evolution of this field and focus on the most enabling and general methods for BCPs synthesis, considering both scope and limitation. Recent breakthroughs on the synthesis of bridge-substituted BCPs are described, as well as methodologies for postsynthesis functionalization. We further explore new challenges and directions for the field, such as the emergence of other rigid small ring hydrocarbons and heterocycles possessing unique substituent exit vectors.

Publication status:: Published

Peer review status:: Peer reviewed

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APA Style

Shire, B. R., & Anderson, E. A. (2023). Conquering the synthesis and functionalization of bicyclo[1.1.1]pentanes. JACS Au, 3(6), 1539–1553.

MLA Style

Shire, B. R., and E. A. Anderson. “Conquering the Synthesis and Functionalization of Bicyclo[1.1.1]Pentanes.” JACS Au, vol. 3, no. 6, American Chemical Society, 2023, pp. 1539–53.

Chicago Style

Shire, BR, and EA Anderson. 2023. “Conquering the Synthesis and Functionalization of Bicyclo[1.1.1]Pentanes.” JACS Au 3 (6): 1539–53.
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Files:: Shire_and_Anderson_2023_Conquering_the_synthesis.pdf

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Publisher copy:: 10.1021/jacsau.3c00014

Authors

+ Shire, BR More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Organic Chemistry
Role:: Author

+ Anderson, EA More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Organic Chemistry
Oxford college:: Jesus College
Role:: Author
ORCID:: 0000-0002-4149-0494

+ Engineering and Physical Sciences Research Council More from this funder

Funder identifier:: https://ror.org/0439y7842
Grant:: EP/T517811/1; EP/S013172/1

Publisher:: American Chemical Society
Journal:: JACS Au More from this journal
Volume:: 3
Issue:: 6
Pages:: 1539-1553
Place of publication:: United States
Publication date:: 2023-05-16
Acceptance date:: 2023-03-31
DOI:: 10.1021/jacsau.3c00014
EISSN:: 2691-3704
Pmid:: 37388694

Language:: English
Keywords:: bicyclo[1.1.1]pentane

photoredox catalysis

bioisostere

radical reactions

[1.1.1]propellane
Subtype:: Review
Pubs id:: 1469360
Local pid:: pubs:1469360
Deposit date:: 2024-06-24

Terms of use

Copyright holder:: Shire and Anderson
Copyright date:: 2023
Rights statement:: © 2023 The Authors. Published by American Chemical Society. This publication is licensed under CC-BY 4.0.

Licence:: CC Attribution (CC BY)

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