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

被引：56

作者：

Alaimo, Peter J. ^{[1
]}

O'Brien, Robert ^{[1
]}

Johnson, Adam W. ^{[1
]}

Slauson, Sarah R. ^{[1
]}

O'Brien, Jeannette M. ^{[1
]}

Tyson, Elizabeth L. ^{[1
]}

Marshall, Amanda-Lynn ^{[1
]}

Ottinger, Colleen E. ^{[1
]}

Chacon, Jon G. ^{[1
]}

Wallace, Lorien ^{[1
]}

Paulino, Corey Y. ^{[1
]}

Connell, Sarah ^{[1
]}

机构：

[1] Seattle Univ, Dept Chem, Seattle, WA 98122 USA

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 22期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1021/ol801911f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：5111 / 5114

页数：4

共 28 条

[1] Bronsted acid-catalyzed aza Diels-Alder reaction of Danishefsky's diene with aldimine generated in situ from aldehyde and amine in aqueous media [J].