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DBU‐Catalyzed Glutamation of Phenols, Thiophenols, Secondary Amines and Imides
European Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2024-04-26 , DOI: 10.1002/ejoc.202400184
Xue-Ying Wang 1 , Si-Kai Zhu 1 , Mei-Ling Cheng 1 , Ru Jiang 1 , Sheng-Yong Zhang 1 , Ping-An Wang 2
Affiliation  

1,8‐Diazabicyclo[5.4.0]undec‐7‐ene (DBU) catalyzed Michael additions between α,β‐unsaturated esters and benzophenone‐imine of glycine esters in THF at room temperature by using LiBr as an additive for glutamation of phenols, thiophenols, secondary amines and imides have been realized. 3‐Substituted glutamic acid esters were obtained in excellent yields and diastereoselectivities (up to quant. yield and > 20:1 d.r.). These glutamic acid esters were easily converted into their corresponding pyroglutamic acid esters in high yields through acidic hydrolysis followed lactamation.

中文翻译:

DBU 催化苯酚、硫酚、仲胺和酰亚胺的谷氨酸化

室温下,1,8-二氮杂双环[5.4.0]十一碳-7-烯 (DBU) 催化甘氨酸酯的 α,β-不饱和酯与二苯甲酮亚胺在 THF 中进行迈克尔加成,使用溴化锂作为酚类谷氨酸化添加剂、苯硫酚、仲胺和酰亚胺已实现。 3-取代的谷氨酸酯以优异的产率和非对映选择性(高达定量产率和 > 20:1 dr)获得。这些谷氨酸酯很容易通过酸水解和内酰胺化以高产率转化为相应的焦谷氨酸酯。
更新日期:2024-04-26
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