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Sustainable synthetic methods: domino construction of dihydropyridin-4-ones and beta-amino esters in aqueous ethanol |
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| 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 |
| Affiliation: | Department of Chemistry, Seattle University, Seattle, Washington 98122, USA. alaimop@seattleu.edu |
| Abstract: | 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 In(0) generates an amine and In (III) byproducts. Addition of aldehyde followed by Danishefsky's diene or silyl ketene acetal provides access to dihydropyridin-4-ones or beta-amino esters, respectively, in yields that are comparable or superior to the reported stepwise reactions. |
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