Journal article

Synthesis and applications of highly functionalized 1-halo-3-substituted bicyclo[1.1.1]pentanes

Abstract:: Bicyclo[1.1.1]pentanes (BCPs) are important bioisosteres of 1,4-disubstituted arenes, tert-butyl and acetylenic groups that can impart physicochemical benefits on drug candidates. Here we describe the synthesis of BCPs bearing carbon and halogen substituents under exceptionally mild reaction conditions, via triethylborane-initiated atom-transfer radical addition ring-opening of tricyclo[1.1.1.01,3]pentane (TCP) with alkyl halides. This chemistry displays broad substrate scope and functional group tolerance, enabling application to BCP analogues of biologically-relevant targets such as peptides, nucleosides, and pharmaceuticals. The BCP halide products can be converted to the parent phenyl/tert-butyl surrogates through triethylborane-promoted dehalogenation, or to other derivatives including carbonyls, alcohols, and heterocycles.

Publication status:: Published

Peer review status:: Peer reviewed

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APA Style

Caputo, D., Arroniz, C., Dürr, A., Mousseau, J., Stepan, A., Mansfield, S., & Anderson, E. (2018). Synthesis and applications of highly functionalized 1-halo-3-substituted bicyclo[1.1.1]pentanes. Chemical Science, 9(23), 5295–5300 .

MLA Style

Caputo, D., et al. “Synthesis and Applications of Highly Functionalized 1-Halo-3-Substituted Bicyclo[1.1.1]Pentanes.” Chemical Science, vol. 9, no. 23, Royal Society of Chemistry, 2018, pp. 5295–300 .

Chicago Style

Caputo, D, C Arroniz, A Dürr, J Mousseau, A Stepan, S Mansfield, and E Anderson. 2018. “Synthesis and Applications of Highly Functionalized 1-Halo-3-Substituted Bicyclo[1.1.1]Pentanes.” Chemical Science 9 (23): 5295–5300 .
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Files:: Caputo_2018_synthesis_and_applications.pdf

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Publisher copy:: 10.1039/C8SC01355A

Authors

+ Caputo, D More by this author

Institution:: University of Oxford
Division:: MPLS Division
Department:: Chemistry; Organic Chemistry
Role:: Author
ORCID:: 0000-0002-5821-1965

+ Arroniz, C More by this author

Institution:: University of Oxford
Division:: MPLS Division
Department:: Chemistry; Organic Chemistry
Role:: Author
ORCID:: 0000-0002-3513-8267

+ Dürr, A More by this author

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

+ Mousseau, J More by this author

Role:: Author

+ Stepan, A More by this author

Role:: Author

More authors...

+ Engineering and Physical Sciences Research Council More from this funder

Funding agency for:: Arroniz, C; Caputo, D; Mansfield, S; Anderson, E
Grant:: EP/M019195/1; EP/L015838/1; EP/L015838/1; EP/M019195/1

+ Heinrich Hertz Foundation More from this funder

Funding agency for:: Dürr, A

Publisher:: Royal Society of Chemistry
Journal:: Chemical Science More from this journal
Volume:: 9
Issue:: 23
Pages:: 5295-5300
Publication date:: 2018-05-21
Acceptance date:: 2018-05-20
DOI:: 10.1039/C8SC01355A
EISSN:: 2041-6539
ISSN:: 2041-6520

Pubs id:: pubs:858456
UUID:: uuid:22098225-945d-4121-9683-5c44f6df7334
Local pid:: pubs:858456
Source identifiers:: 858456
Deposit date:: 2018-06-20

Terms of use

Copyright holder:: © Caputo, et al
Copyright date:: 2018
Notes:: This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.

Licence:: CC Attribution (CC BY)

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