通过碳亲核试剂对吲哚啉中间体的共轭加成实现羧化哌嗪 -2,5 -二酮与吲哚的直接有机催化偶联反应。
Direct organocatalytic coupling of carboxylated piperazine-2,5-diones with indoles through conjugate addition of carbon nucleophiles to indolenine intermediates.
作者信息
Dubey Ramin, Olenyuk Bogdan
机构信息
Department of Chemistry and Biochemistry, The University of Arizona, Tucson, AZ 85721.
出版信息
Tetrahedron Lett. 2010 Jan 27;51(4):609-612. doi: 10.1016/j.tetlet.2009.11.068.
Abstract
The indole-diketopiperazine bridge is an important structural feature of many bispyrrolidinoindoline and epipolythiodiketopiperazine fungal metabolites. Organocatalytic conjugate addition of diketopiperazines to indoles was achieved in good to excellent yields through electrophilic indolenine intermediates generated under mild conditions. Screening of catalysts and solvents at different temperatures was performed in order to achieve high product yields.
摘要
吲哚-二酮哌嗪桥是许多双吡咯烷基吲哚啉和表聚硫代二酮哌嗪真菌代谢产物的重要结构特征。通过在温和条件下生成的亲电吲哚宁中间体，实现了二酮哌嗪对吲哚的有机催化共轭加成，产率良好至优异。为了获得高产物产率，在不同温度下对催化剂和溶剂进行了筛选。
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