Microreactor-Mediated Organocatalysis: Towards the Development of Sustainable Domino Reactions

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J. Flow Chem. 2013, 3, (2), pp 29-33

Laura Carroccia1, Biagia Musio1, Leonardo Degennaro1, Giuseppe Romanazzi2 and Renzo Luisi1
1Department of Pharmacy, University of Bari “A. Moro,” Via E. Orabona 4, Bari 70125, Italy
22DICATECh, Polytechnic of Bari, Via E. Orabona 4, Bari 70125, Italy

This paper describes the microfluidic optimisation of a two-step strategy for the manufacture of a range of bicyclodecanes with six contiguous stereogenic centres. This paper further describes the optimisation of an organocatalysed Michael addition, giving highly diastereoselective γ-nitroketones which were further telescoped into a nitro-Michael-aldol reaction to yield the bicyclo[4.4.0]decanes with enantiomeric ratios of up to 89:11.

Abstract: Microreactor-mediated organocatalysed Michael reactions have been developed. By using a soluble proline-derived catalyst, Michael-type reactions, leading to γ-nitroketones, have been optimized in homogeneous and continuous-flow conditions. As proof of principle, an integrated microfluidic system able to perform domino processes useful in the preparation of bicyclo[4.4.0]decanes with six contiguous stereogenic centres has been set up.

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This paper uses an Asia flow chemistry system.