In this work, we describe the use of Boron Dipyrromethene (BODIPY) as electron‐withdrawing group for activation of double bonds in asymmetric copper‐catalyzed [3+2] cycloaddition reactions with azomethine ylides. The reactions take place under smooth conditions and with high enantiomeric excess for a large number of different substituents, pointing out the high activation of the alkene by using a boron dipyrromethene as electron‐withdrawing group. Experimental, theoretical studies and comparison with other common electron‐withdrawing groups in asymmetric copper‐catalyzed [3+2] cycloadditions show the reasons of the different reactivity of the boron dipyrromethene derivatives, which can be exploited as a useful activating group in asymmetric catalysis. Additional experiments show that the so obtained pyrrolidines can be employed as biocompatible biosensors, which can be located in the endosomal compartments and do not present toxicity in three cell lines.

中文翻译：

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硼二吡咯亚甲基（BODIPY）作为不对称铜催化的[3 + 2]环加成物中的吸电子基团，用于合成基于吡咯烷的生物传感器

在这项工作中，我们描述了使用硼二吡咯亚甲基（BODIPY）作为吸电子基团，以在不对称铜催化的[3 + 2]偶氮甲亚胺基环加成反应中激活双键。该反应在光滑的条件下进行，对于大量不同的取代基而言，其对映体过量很高，这表明使用硼二吡咯亚甲基作为吸电子基团可以高度活化烯烃。实验，理论研究以及与不对称铜催化的[3 + 2]环加成物中其他常见的吸电子基团的比较表明，硼二吡咯亚甲基衍生物的反应性不同的原因可以用作不对称催化中的有用活化基。