Diels-alder reactions of N-acyl-2-alkyl(aryl)-5-vinyl-2,3-dihydro-4-pyridones

被引：38

作者：

Comins, DL ^{[1
]}

Kuethe, JT ^{[1
]}

Miller, TM ^{[1
]}

Février, FC ^{[1
]}

Brooks, CA ^{[1
]}

机构：

[1] N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 13期

关键词：

D O I：

10.1021/jo050559n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Readily available N-acyl-5-vinyl-2,3-dihydro-4-pyridones undergo Diels-Alder cyclization with various dienophiles to afford novel octahydroquinolines containing synthetically useful functionality. With dihydropyridone 5 and cis-disubstituted dienophiles, the resulting cycloadducts were obtained as single diastereomers in good to excellent yield. The corresponding reaction of 5 with methyl acrylate, acrylonitrile, and phenyl vinyl sulfone showed modest preference for the endo adducts. The effect of the dihydropyridone C-2 and C-4 substituents on the degree of diastereofacial control was examined. By using this methodology, the core decahydroquinoline skeleton of gephyrotoxin was prepared in a stereocontrolled fashion. Interesting reactivity was observed with certain dienophiles leading to ring-opening of the initially formed cycloadducts. This tandem reaction provides a route to uniquely substituted beta-aminoketones, alcohols, and unnatural amino acids.

引用

页码：5221 / 5234

页数：14

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