A Recyclable Chiral 2‐(Triphenylmethyl)pyrrolidine Organocatalyst Anchored to [60]Fullerene

Abstract

Hybridization of a chiral 3‐hydroxy‐2‐trityl‐pyrrolidine deriving from (R)‐pyrrolidinol with [60]fullerene via click chemistry provides a highly efficient supported enantioselective organocatalyst, which was successfully exploited in a Michael addition of malonates to cinnamaldehydes, via iminium ion activation. The supported organocatalyst was recycled up to six times, with only a moderate decrease in terms of activity and with no loss in enantioselectivity.magnified image

Mapping the Surface Groups of Amine-Rich Carbon Dots Enables Covalent Catalysis in Aqueous Media

“…68 So far, the use of carbon nanomaterials in enantioselective transformations has only been addressed relying on post-functionalization procedures. 69,70 While, due to the harsh synthetic reaction conditions, the enantiopure building blocks undergo racemization generally leading to optically inactive CDs, as in the case of NCDs-1, 17 recently, chiral NCDs (NCDs-7) have been successfully prepared by employing (R,R)-or (S,S)-1,2-cyclohexanediamine in combination with L-arginine as precursors (Figure 8A). 17 Therefore, we studied the catalytic behavior of (S)-NCDs-7 in the aldol addition of acetone 1e to isatin 5a under enamine catalysis conditions (Figure 8B; Table S2).…”

Amino-Functionalized Cage-Opened C60 Derivatives

“…These amino-functionalized C 60 derivatives have been demonstrated to exhibit antiviral and antibacterial activities . In addition, they could be utilized as organocatalysts and stoppering units in mechanically interlocked molecules, as well as n-type materials in photovoltaic devices …”

Synthesis and applications of amino-functionalized carbon nanomaterials

“…After six catalytic cycles, only a minor loss of catalytic performance was observed, with unaltered enantioselectivity. 76 Many applications of fullerenes functionalized with the 1,3dipolar cycloaddition in energy related fields have been reported, mainly because of the excellent optoelectronic properties of the carbon sphere. 77 C60 has a favorable band-gap (2.3 eV in the solid state) and an n-type material character: 78 because of these features this scaffold was extensively used in the fabrication of photovoltaic devices.…”