Journal article
Hydrogen borrowing catalysis using 1° and 2° alcohols: investigation and scope leading to α and β branched products
- Abstract:
- The alkylation of a variety of ketones using 1° or 2° alcohols under hydrogen borrowing catalysis is described. Initial research focused on the α-alkylation of cyclopropyl ketones with higher 1° alcohols (i.e. larger than MeOH), leading to the formation of α-branched products. Our search for additional substrates with which to explore this chemistry led us to discover that di-ortho-substituted aryl ketones were also privileged scaffolds, with Ph∗ (C6Me5) ketones being the optimal choice. Further investigations revealed that this motif was crucial for alkylation with 2° alcohols forming β-branched products, which also provided an opportunity to study diastereoselective and intramolecular hydrogen borrowing processes.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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- Files:
-
-
(Preview, Accepted manuscript, pdf, 2.4MB, Terms of use)
-
- Publisher copy:
- 10.1016/j.tet.2021.132051
Authors
- Publisher:
- Elsevier
- Journal:
- Tetrahedron More from this journal
- Volume:
- 86
- Article number:
- 132051
- Publication date:
- 2021-03-05
- Acceptance date:
- 2021-02-19
- DOI:
- ISSN:
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0040-4020
- Language:
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English
- Keywords:
- Pubs id:
-
1162422
- Local pid:
-
pubs:1162422
- Deposit date:
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2021-02-19
- ARK identifier:
Terms of use
- Copyright holder:
- Elsevier Ltd
- Copyright date:
- 2021
- Rights statement:
- © 2021 Elsevier Ltd. All rights reserved.
- Notes:
- This is the accepted manuscript version of the article. The final version is available online from Elsevier at: https://doi.org/10.1016/j.tet.2021.132051
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