Publication – Microreactor-mediated organocatalysis: Towards the development of sustainable domino reactions

J. Flow Chem. 2013, 3, (2), pp 29-33

Laura Carroccia¹, Biagia Musio¹, Leonardo Degennaro¹, Giuseppe Romanazzi² and Renzo Luisi^1
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.

This paper uses an Asia flow chemistry system.