Sustainable Synthetic Methods: Domino Construction of Dihydropyridin-4-ones and β-Amino Esters in Aqueous Ethanol

Domino reactions were designed to allow the byproduct of an upstream reaction to be internally recycled to catalyze a downstream reaction in a one-pot tandem sequence. Nitroarene reduction by In0 generates an amine and InIII byproducts. Addition of aldehyde followed by Danishefsky’s diene or silyl k...

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Bibliographic Details
Published in:Organic letters 2008-11, Vol.10 (22), p.5111-5114
Main Authors: Alaimo, Peter J, O’Brien, Robert, Johnson, Adam W, Slauson, Sarah R, O’Brien, Jeannette M, Tyson, Elizabeth L, Marshall, Amanda-Lynn, Ottinger, Colleen E, Chacon, Jon G, Wallace, Lorien, Paulino, Corey Y, Connell, Sarah
Format: Article
Language:English
Subjects:
Catalysis
Dihydropyridines - chemical synthesis
Dihydropyridines - chemistry
Esters - chemical synthesis
Esters - chemistry
Ethanol - chemistry
Green Chemistry Technology
Water - chemistry
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Summary:Domino reactions were designed to allow the byproduct of an upstream reaction to be internally recycled to catalyze a downstream reaction in a one-pot tandem sequence. Nitroarene reduction by In0 generates an amine and InIII byproducts. Addition of aldehyde followed by Danishefsky’s diene or silyl ketene acetal provides access to dihydropyridin-4-ones or β-amino esters, respectively, in yields that are comparable or superior to the reported stepwise reactions.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol801911f