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Synfacts 2015; 11(1): 0083
DOI: 10.1055/s-0034-1379650
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Oxidative Amination of the Zinc Bromide Complex of β-Enamino Esters

Contributor(s):
Paul Knochel
,
Diana Haas
Kim JH, Choi SY, Bouffard J, Lee S.-g * Ewha Womans University, Seoul, Republic of Korea
Tandem One-Pot Synthesis of Polysubstituted NH-Pyrroles Involving the Palladium-Catalyzed Intramolecular Oxidative Amination of the Zinc Bromide Complex of β-Enamino Esters.

J. Org. Chem. 2014;
79: 9253-9261
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Publication History

Publication Date:
15 December 2014 (online)

 
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Key words

amination - zinc - pyrroles

Significance

Lee and co-workers report a tandem palladium-catalyzed intramolecular oxidative olefin amination of the zinc bromide complex of α-vinylated β-amino esters to afford various 2,3,4-trisubstituted pyrroles in good yields.


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Comment

The synthetic utility of this efficient and atom-economical procedure is shown by the synthesis of pyrrolophenanthrenes and pyranopyrrolones through selective palladium- and copper-catalyzed C–C and C–O bond-forming reactions.


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