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An enamine controlling group for rhodium-catalyzed intermolecular hydroacylation

Abstract:
An enamine-controlled hydroacylation of alkynes using a rhodium(I)/dppe catalyst system is described. The reaction is highly selective, forming the linear enaminone products as single regioisomers in all examples. In situ hydrolysis of the enamine functionality generated α-substituted 1,3-diketone products, and Lewis-acid mediated intramolecular conjugate addition of the hydroacylation products gave substituted hexahydroquinolones.
Publication status:
Published
Peer review status:
Peer reviewed
Version:
Accepted Manuscript

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Publisher copy:
10.1016/j.tet.2018.04.068

Authors


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Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry; Organic Chemistry
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Lupton, JD More by this author
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry; Organic Chemistry
Oxford college:
Lincoln College
ORCID:
0000-0002-0636-6471
Publisher:
Elsevier Publisher's website
Journal:
Tetrahedron Journal website
Volume:
74
Issue:
38
Pages:
5408-5414
Publication date:
2018-04-25
Acceptance date:
2018-04-20
DOI:
ISSN:
0040-4020
Pubs id:
pubs:847896
URN:
uri:b6119d6f-e517-4cec-9011-1056c00d45cb
UUID:
uuid:b6119d6f-e517-4cec-9011-1056c00d45cb
Local pid:
pubs:847896

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