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烯醇酯：用于曼尼希型多组分反应的通用底物。

Enol esters: versatile substrates for Mannich-type multicomponent reactions.

作者信息

Isambert Nicolas, Cruz Montse, Arévalo María José, Gómez Elena, Lavilla Rodolfo

机构信息

Institute for Research in Biomedicine, Barcelona Science Park, Josep Samitier 1-5, 08028 Barcelona, Spain.

出版信息

Org Lett. 2007 Oct 11;9(21):4199-202. doi: 10.1021/ol701717z. Epub 2007 Sep 15.

DOI:10.1021/ol701717z
PMID:17867693
Abstract

The interaction of cyclic enol esters with diversely substituted anilines and ethyl glyoxalate yields, under Sc(OTf)3 catalysis, disubstituted N-aryl lactams in a multicomponent reaction. The protocol allows access to the trans stereoisomers after an epimerization of the initial mixture in which the cis isomers predominate. Vinyl acetate yields quinoline derivatives, whereas isopropenyl acetate leads to the corresponding Mannich adducts.

摘要

在三氟甲磺酸钪催化下，环状烯醇酯与不同取代的苯胺和乙醛酸乙酯相互作用，通过多组分反应生成二取代的N-芳基内酰胺。该方法能够在初始混合物（其中顺式异构体占主导）进行差向异构化后得到反式立体异构体。乙酸乙烯酯生成喹啉衍生物，而乙酸异丙烯酯则生成相应的曼尼希加合物。

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