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

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• 作者：Peter J. Alaimo ; Robert O&#8217 ; Brien ; ; Adam W. Johnson ; Sarah R. Slauson ; Jeannette M. O&#8217 ; Brien ; Elizabeth L. Tyson ; Amanda-Lynn Marshall ; Colleen E. Ottinger ; Jon G. Chacon ; Lorien Wallace ; Co
• 刊名：Organic Letters
• 出版年：2008
• 出版时间：November 20, 2008
• 年：2008
• 卷：10
• 期：22
• 页码：5111-5114
• 全文大小：134K
• 年卷期：v.10,no.22(November 20, 2008)
• ISSN：1523-7052

文摘

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 In^III 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.