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A short synthesis of 3-enoyltetramic acids employing a new acyl ylide conjugate of Meldrum’s acid
Tetrahedron Letters ( IF 1.8 ) Pub Date : 2017-11-13 , DOI: 10.1016/j.tetlet.2017.11.025
Kevin Lovmo , Steffen Dütz , Marina Harras , Robert G. Haase , Wolfgang Milius , Rainer Schobert

2,2-Dimethyl-5-(triphenylphosphoranylidene)acetyl-1,3-dioxan-4,6-dione (3) is a new activated β-ketoacyl equivalent, readily prepared in quantitative yield by reaction of Meldrum’s acid with the stable ylide Ph3PCCO. Its reaction with α-amino esters affords the corresponding N-(β-ketoacyl)amino ester ylides which, when treated with aldehydes and KOtBu, undergo a simultaneous Wittig olefination cum Dieckmann cyclisation to yield the respective 3-enoyltetramic acids.



中文翻译:

使用Meldrum酸的新酰基内酯共轭物快速合成3-enoyltetramic酸

2,2-二甲基-5-(三苯基正膦亚基)乙酰基-1,3-二恶烷-4,6-二酮(3)是一种新的活化的β-酮酰基当量,易于通过Meldrum酸与稳定的叶立德反应以定量收率制得Ph 3 PCCO。它与α氨基酯反应,得到相应的Ñ - (β酮酰基)氨基酯叶立德,当与醛和KO处理卜,经历同时Wittig烯化暨迪克曼环化,得到相应的3- enoyltetramic酸。

更新日期:2017-11-13
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