Journal article
Synthesis of enantioenriched α-chiral bicyclo[1.1.1]pentanes
- Abstract:
- Bicyclo[1.1.1]pentanes (BCPs), useful surrogates for para-substituted arenes, alkynes, and tert-butyl groups in medicinal chemistry, are challenging to prepare when featuring stereogenic centers adjacent to the BCP. We report the development of an efficient route to α-chiral BCPs, via highly diastereoselective asymmetric enolate functionalization. We also describe the application of this chemistry to the synthesis of BCP analogues of phenylglycine and tarenflurbil, the single enantiomer of the NSAID flurbiprofen.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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- Files:
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(Preview, Accepted manuscript, pdf, 617.5KB, Terms of use)
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- Publisher copy:
- 10.1021/acs.orglett.9b00691
Authors
- Publisher:
- American Chemical Society
- Journal:
- Organic Letters More from this journal
- Volume:
- 21
- Issue:
- 7
- Pages:
- 2408-2411
- Publication date:
- 2019-03-14
- Acceptance date:
- 2019-03-14
- DOI:
- EISSN:
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1523-7052
- ISSN:
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1523-7060
- Pmid:
-
30869907
- Language:
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English
- Keywords:
- Pubs id:
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pubs:983441
- UUID:
-
uuid:0b13041e-08a3-4ba1-8f47-69143e87fcb5
- Local pid:
-
pubs:983441
- Source identifiers:
-
983441
- Deposit date:
-
2019-05-17
- ARK identifier:
Terms of use
- Copyright holder:
- American Chemical Society
- Copyright date:
- 2019
- Rights statement:
- © 2019 American Chemical Society. A correction to this article is available online from the American Chemical Society at: https://doi.org/10.1021/acs.orglett.9b01503
- Notes:
- This is the accepted manuscript version of the article. The final version is available online from the American Chemical Society at: https://doi.org/10.1021/acs.orglett.9b00691
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