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  • Author or Editor: Sergio Rossi x
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Metal-free stereoselective additions of activated nucleophiles to β-nitrostyrenes were investigated under continuous-flow conditions in microreactors, in the presence of a chiral bifunctional catalyst. Optimization of the experimental setup gave excellent enantioselectivities (up to 85% e.e.) and higher productivities if compared to the flask syntheses. The potential of this flow chemistry approach was demonstrated by the successful synthesis of an advanced intermediate for the preparation of the GABAB receptor agonist Baclofen.

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The Sandmeyer reaction of anilines to generate aryl azides, followed by the Ru(porphyrin)CO-catalyzed addition to styrenes affording N-aryl aziridines was successfully performed for the first time in mesoreactors, under continuousflow conditions. Mesofluidic technology allowed for a rapid screening of different parameters and a quick identification of the optimized reaction conditions for the two separate steps. The two optimized reactions were then combined in a single continuous process that allowed a safe and efficient synthesis of N-arylaziridines from convenient commercially available starting materials.

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