126079-16-1Relevant articles and documents
Dynamic Catalytic Highly Enantioselective 1,3-Dipolar Cycloadditions
Antonchick, Andrey P.,Brieger, Lukas,Grigalunas, Michael,Strohmann, Carsten,Waldmann, Herbert,Yildirim, Okan
, p. 20012 - 20020 (2021)
In dynamic covalent chemistry, reactions follow a thermodynamically controlled pathway through equilibria. Reversible covalent-bond formation and breaking in a dynamic process enables the interconversion of products formed under kinetic control to thermod
Copper/GanPhos-Catalyzed 1,3-Dipolar Cycloaddition of Azo?-methine Ylides: An Efficient Access to Chiral Pyrrolidine Spirocycles
Gan, Zhenjie,Li, Ke,Zhang, Hui,Li, Er-Qing
supporting information, p. 1331 - 1340 (2020/11/30)
A highly efficient copper/GanPhos-catalyzed 1,3-dipolar cyclo?-addition?-of azomethine ylides is reported. This viable transformation provides a series of optically active spiro[dihydronaphthalene-2,3′-pyrrolidine]s, bearing one spiro quaternary and three tertiary stereogenic centers, in good yields and with high ee values. This protocol features high diastereo- A nd enantioselectivity, broad substrate scope and mild reaction conditions.
Boron Dipyrromethene (BODIPY) as Electron-Withdrawing Group in Asymmetric Copper-Catalyzed [3+2] Cycloadditions for the Synthesis of Pyrrolidine-Based Biological Sensors
Alemán, José,Asenjo-Pascual, Juan,Cordani, Marco,Díaz-Tendero, Sergio,Fraile, Alberto,Martín-Somer, Ana,Milán Rois, Paula,Rigotti, Thomas,Somoza, álvaro
supporting information, (2020/02/20)
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. (Figure presented.).