Journal article
Twofold radical-based synthesis of N,C-difunctionalized bicyclo[1.1.1]pentanes
- Abstract:
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Bicyclo[1.1.1]pentylamines (BCPAs) are of growing importance to the pharmaceutical industry as sp3-rich bioisosteres of anilines and N-tert-butyl groups. Here we report a facile synthesis of 1,3-disubstituted BCPAs using a twofold radical functionalization strategy. Sulfonamidyl radicals, generated through fragmentation of α-iodoaziridines, undergo initial addition to [1.1.1]propellane to afford iodo-BCPAs; the newly formed C–I bond in these products is then functionalized via a silyl-mediated Giese reaction. This chemistry also translates smoothly to 1,3-disubstituted iodo-BCPs. A wide variety of radical acceptors and iodo-BCPAs are accommodated, providing straightforward access to an array of valuable aniline-like isosteres.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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- Files:
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(Preview, Accepted manuscript, 1.8MB, Terms of use)
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- Publisher copy:
- 10.1021/jacs.1c04180
Authors
- Publisher:
- American Chemical Society
- Journal:
- Journal of the American Chemical Society More from this journal
- Volume:
- 143
- Issue:
- 26
- Pages:
- 9729-9736
- Publication date:
- 2021-06-23
- Acceptance date:
- 2021-06-23
- DOI:
- EISSN:
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1520-5126
- ISSN:
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0002-7863
- Pmid:
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34161076
- Language:
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English
- Keywords:
- Pubs id:
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1183945
- Local pid:
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pubs:1183945
- Deposit date:
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2021-07-13
Terms of use
- Copyright holder:
- American Chemical Society
- Copyright date:
- 2021
- Rights statement:
- Copyright © 2021 American Chemical Society
- Notes:
-
This is the accepted manuscript version of the article. The final version is available from American Chemical Society at https://doi.org/10.1021/jacs.1c04180
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