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Boron Dipyrromethene (BODIPY) as Electron‐Withdrawing Group in Asymmetric Copper‐Catalyzed [3+2] Cycloadditions for the Synthesis of Pyrrolidine‐Based Biological Sensors

2020; Wiley; Volume: 362; Issue: 6 Linguagem: Inglês

10.1002/adsc.201901465

1615-4169

Thomas Rigotti, Juan Asenjo‐Pascual, Ana Martín‐Sómer, Paula Milán-Rois, Marco Cordani, Sergio Díaz‐Tendero, Álvaro Somoza, Alberto Fraile, José Alemán,

Molecular Sensors and Ion Detection

Abstract 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. magnified image