Journal article
Diastereoselective ammonium-directed epoxidation in the asymmetric syntheses of dihydroconduramines (+)-C-2, (−)-C-2, (+)-D-2, (+)-E-2, (+)-F-2, and (−)-F-2
- Abstract:
-
Epoxidations (40% aq HBF4 then m-CPBA) of racemic cis-2-(N-benzylamino)cyclohex-3-en-1-ol and racemic cis-2-(N,N-dibenzylamino)cyclohex-3-en-1-ol proceed with very high levels of diastereoselectivity (>95:5 dr). The latter is in direct contrast to the epoxidation of the corresponding trans-diastereoisomer (which proceeds with essentially no selectivity), showing that the relative configuration of the substrate dramatically influences the diastereoselectivity in these instances. Meanwhile, ...
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- Publication status:
- Published
- Peer review status:
- Peer reviewed
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Authors
Bibliographic Details
- Publisher:
- American Chemical Society Publisher's website
- Journal:
- Journal of Organic Chemistry Journal website
- Volume:
- 83
- Issue:
- 17
- Pages:
- 9939–9957
- Publication date:
- 2018-07-24
- Acceptance date:
- 2018-07-24
- DOI:
- EISSN:
-
1520-6904
- ISSN:
-
0022-3263
- Pmid:
-
30037221
Item Description
- Language:
- English
- Pubs id:
-
pubs:905073
- UUID:
-
uuid:6b9a7e65-3562-46d3-aa56-1ccbfeef0518
- Local pid:
- pubs:905073
- Source identifiers:
-
905073
- Deposit date:
- 2018-08-30
Terms of use
- Copyright holder:
- American Chemical Society
- Copyright date:
- 2018
- Notes:
- Copyright © 2018 American Chemical Society. This is the accepted manuscript version of the article. The final version is available online from American Chemical Society at: https://doi.org/10.1021/acs.joc.8b01359
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