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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
Author(s) -
Rigotti Thomas,
AsenjoPascual Juan,
MartínSomer Ana,
Milán Rois Paula,
Cordani Marco,
DíazTendero Sergio,
Somoza Álvaro,
Fraile Alberto,
Alemán José
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201901465
Subject(s) - chemistry , bodipy , cycloaddition , polar effect , pyrrolidine , boron , alkene , combinatorial chemistry , catalysis , reactivity (psychology) , copper , photochemistry , organic chemistry , fluorescence , physics , quantum mechanics , medicine , alternative medicine , pathology
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.