Quinine Derivative

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Miquel A Pericas - One of the best experts on this subject based on the ideXlab platform.

Alessandra Puglisi - One of the best experts on this subject based on the ideXlab platform.

  • solid supported 9 amino 9 deoxy epi Quinine as efficient organocatalyst for stereoselective reactions in batch and under continuous flow conditions
    Advanced Synthesis & Catalysis, 2015
    Co-Authors: Riccardo Porta, Maurizio Benaglia, Francesca Coccia, Franco Cozzi, Alessandra Puglisi
    Abstract:

    Polystyrene-supported 9-amino-9-deoxy-epi-Quinine was synthesized through co-polymerization of an ad hoc-designed chiral monomer with divinylbenzene, in the presence of azobis(isobutyronitile) (AIBN) as radical initiator and toluene and 1-dodecanol as porogenic solvents. The heterogenized catalyst efficiently promoted the reaction of isobutyric aldehyde with β-nitrostyrene, in very high yield and enantioselectivity, comparable or even higher than that of the homogeneous counterpart (up to 95% ee). The recyclability of the catalyst, its general applicability and its successful application to other reactions was also demonstrated. Finally, for the first time, a 9-amino-epi-Quinine Derivative was employed to perform an enantioselective Michael reaction under continuous-flow conditions; by using a home-made, packed-bed catalytic reactor, the aldehyde addition to nitrostyrene was successfully realized in flow mode, leading to the product in up to 93% ee.

Javier Izquierdo - One of the best experts on this subject based on the ideXlab platform.

Carles Ayats - One of the best experts on this subject based on the ideXlab platform.

Andrea H Henseler - One of the best experts on this subject based on the ideXlab platform.