Cu(OTf)2‑Catalyzed Synthesis of 2,3-Disubstituted Indoles and 2,4,5-Trisubstituted Pyrroles from α‑Diazoketones

A novel method has been devised for the synthesis of 2,4,5-trisubstituted pyrrole derivatives through the coupling of α-diazoketones with β-enaminoketones and esters using 10 mol % of Cu(OTf)2. A wide range of 2,3-disubstituted indole derivatives were also prepared from α-diazoketones and 2-aminoary...

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Bibliographic Details
Published in:Organic letters 2013-02, Vol.15 (3), p.464-467
Main Authors: Reddy, B. V. Subba, Reddy, M. Ramana, Rao, Y. Gopal, Yadav, J. S, Sridhar, B
Format: Article
Language:English
Subjects:
Catalysis
Combinatorial Chemistry Techniques
Indoles - chemical synthesis
Indoles - chemistry
Ketones - chemistry
Mesylates - chemistry
Molecular Structure
Pyrroles - chemical synthesis
Pyrroles - chemistry
Stereoisomerism
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Summary:A novel method has been devised for the synthesis of 2,4,5-trisubstituted pyrrole derivatives through the coupling of α-diazoketones with β-enaminoketones and esters using 10 mol % of Cu(OTf)2. A wide range of 2,3-disubstituted indole derivatives were also prepared from α-diazoketones and 2-aminoaryl or alkyl ketones. The synthetic versatility of this approach has been exemplified in the formal synthesis of homofascaplysin C.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol303206w