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Synthesis of Exo‐ and Endocyclic Enamides Through Copper‐Catalyzed Regioselective Intramolecular N‐Halovinylation
European Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2020-04-28 , DOI: 10.1002/ejoc.202000137
Nicolas Gilbert 1 , Simon Ricard 1 , Jodrey Bergeron 1 , Pierre Lambolez 1 , Benoit Daoust 1
Affiliation  

The intramolecular copper‐catalyzed cross‐coupling of 1,2‐dihaloalkenes and amides leads to cyclic β‐haloenamides, which can participate in a second cross‐coupling reaction to efficiently synthesize highly functionalized cyclic enamides. The selectivity of the intramolecular coupling between exo‐ and endocyclic regioisomers is a crucial synthetic factor and can be influenced by the structure of the substrate and the reaction conditions.
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中文翻译:

铜催化的区域选择性分子内N-卤代酰化反应合成环外和环内酰胺

1,2-二卤代烯烃与酰胺的分子内铜催化交叉偶联反应生成环状β-卤代烯酰胺,后者可参与第二次交叉偶联反应以有效合成高度官能化的环状酰胺。外环和内环区域异构体之间分子内偶联的选择性是至关重要的合成因素,并受底物结构和反应条件的影响。
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更新日期:2020-04-28
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