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Formal (4+1) Cyclization of Ammonium Ylides with Vinylogous para-Quinone Methides
Synthesis ( IF 2.2 ) Pub Date : 2018-09-05 , DOI: 10.1055/s-0037-1610268
Lukas Roiser 1 , Katharina Zielke 1 , Mario Waser 1
Affiliation  

Abstract

The formal (4+1) cyclization between in situ generated achiral carbonyl-stabilized ammonium ylides and vinylogous p-quinone methides can be carried out under operationally simple conditions, leading to two different double bond regioisomers depending on the conditions used. Apart from these racemic approaches, a first proof-of-concept for enantioselective versions of these reactions was also obtained.

The formal (4+1) cyclization between in situ generated achiral carbonyl-stabilized ammonium ylides and vinylogous p-quinone methides can be carried out under operationally simple conditions, leading to two different double bond regioisomers depending on the conditions used. Apart from these racemic approaches, a first proof-of-concept for enantioselective versions of these reactions was also obtained.



中文翻译:

叶立德铵与乙烯基对醌甲基化物的形式 (4+1) 环化

摘要

原位产生的非手性羰基稳定的铵叶立德和插烯醌甲基化物之间的形式(4+1)环化可以在操作简单的条件下进行,根据使用的条件产生两种不同的双键区域异构体。除了这些外消旋方法外,还获得了这些反应的对映选择性形式的第一个概念验证。

原位产生的非手性羰基稳定的铵叶立德和插烯醌甲基化物之间的形式(4+1)环化可以在操作简单的条件下进行,根据使用的条件产生两种不同的双键区域异构体。除了这些外消旋方法外,还获得了这些反应的对映选择性形式的第一个概念验证。

更新日期:2018-09-05
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