Journal article
Hydrogen borrowing catalysis with secondary alcohols: a new route for the generation of β-branched carbonyl compounds
- Abstract:
- A hydrogen borrowing reaction employing secondary alcohols and Ph* (Me5C6) ketones to give β-branched carbonyl products is described (21 examples). This new C-C bond forming process requires low loadings of [Cp*IrCl2]2, relatively low temperatures, and up to 2.0 equiv of the secondary alcohol. Substrate-induced diastereoselectivity was observed, and this represents the first example of a diastereoselective enolate hydrogen borrowing alkylation. By utilizing the Ph* group, the β-branched products could be straightforwardly cleaved to the corresponding esters or amides using a retro-Friedel-Crafts reaction. Finally, this protocol was applied to the synthesis of fragrance compound (±)-3-methyl-5-phenylpentanol.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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(Preview, Version of record, pdf, 1.7MB, Terms of use)
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- Publisher copy:
- 10.1021/jacs.6b12840
Authors
+ Engineering and Physical Sciences Research Council
More from this funder
- Funding agency for:
- Frost, J
- Donohoe, T
- Grant:
- EP/L023121/1
- EP/L023121/1
- Publisher:
- American Chemical Society
- Journal:
- Journal of the American Chemical Society More from this journal
- Volume:
- 139
- Issue:
- 7
- Pages:
- 2577–2580
- Publication date:
- 2017-02-08
- Acceptance date:
- 2017-02-01
- DOI:
- ISSN:
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1520-5126
- Language:
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English
- Pubs id:
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pubs:679457
- UUID:
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uuid:d662c142-50bb-442d-babf-68d13afb60c4
- Local pid:
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pubs:679457
- Source identifiers:
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679457
- Deposit date:
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2017-02-22
Terms of use
- Copyright holder:
- American Chemical Society
- Copyright date:
- 2017
- Notes:
- Copyright © 2017 American Chemical Society. This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
- Licence:
- CC Attribution (CC BY)
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