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OBO-protected pyruvates as reagents for the synthesis of functionalized heteroaromatic compounds

Abstract:
Pd-catalyzed α-arylation of methyl-OBO-ketone (OBO = 4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl) gives rise to arylated OBO-protected pyruvates. By appropriate prefunctionalization of the aryl ring or by subsequent functionalization at the α-carbonyl position of the arylated OBO-ketones, useful diketo OBO-protected carboxylates can be generated. Cyclization, aromatization, and OBO deprotection of these intermediates, using two distinct routes, gives access to valuable α-acyl heteroaromatic compounds.
Publication status:
Published
Peer review status:
Peer reviewed
Version:
Accepted Manuscript

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Publisher copy:
10.1021/acs.orglett.8b01614

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More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry; Organic Chemistry
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry; Organic Chemistry
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry; Organic Chemistry
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry; Organic Chemistry
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry; Organic Chemistry
Oxford college:
Magdalen College
More from this funder
Funding agency for:
Alves Estaves, CH
Publisher:
American Chemical Society Publisher's website
Journal:
Organic Letters Journal website
Volume:
20
Issue:
13
Pages:
4048–4051
Publication date:
2018-06-15
Acceptance date:
2018-06-12
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
Pubs id:
pubs:857148
URN:
uri:4b36060b-58a4-4e29-86dd-e5a7df6699a8
UUID:
uuid:4b36060b-58a4-4e29-86dd-e5a7df6699a8
Local pid:
pubs:857148

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