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Modular Synthesis of Highly Substituted Pyridines via Enolate α-Alkenylation.

Abstract:

A novel methodology for the synthesis of highly substituted pyridines based on the palladium-catalyzed enolate α-alkenylation of ketones is presented; the formation of aromatic compounds is a new direction for this catalytic C-C bond forming reaction. In the key step, a protected β-haloalkenylaldehyde participates in α-alkenylation with a ketone to afford a 1,5-dicarbonyl surrogate, which then undergoes cyclization/double elimination to the corresponding pyridine product, all in one pot. The ...

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Publication status:
Published
Peer review status:
Peer reviewed
Version:
Accepted Manuscript

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Publisher copy:
10.1021/acs.orglett.5b01312

Authors


More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
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Funding agency for:
Hardegger, LA
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Funding agency for:
Habegger, J
Publisher:
American Chemical Society Publisher's website
Journal:
Organic letters Journal website
Volume:
17
Issue:
13
Pages:
3222–3225
Publication date:
2015-06-05
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
URN:
uuid:eda3fd6d-f8de-4705-b1dc-d0201fcbd1d4
Source identifiers:
528693
Local pid:
pubs:528693
Language:
English

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