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The University of Southampton

Research project: Rios: Organocascade Reactions

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In recent years, the development of new and powerful organocatalytic cascade reactions has emerged as an area of considerable interest. This is because of the advance in the different activation modes in organocatalyisis and the easy prediction of the stereochemical outcome of the reactions. Using organocatalysis we can be able to synthesize very complex scaffolds in one pot reaction bearing several stereocenters and in enantiopure fashion.

In the past few years, our research group has been working on the development of new organocatalytic methodologies for the enantioselective construction of highly complex scaffolds. During our works, we become fascinated by the synthesis of spirocompounds. We applied our knowledge on organocascade reactions in the development of a highly stereoselective synthesis of spirooxindoles1 and spiropyrazolones2,3 via a Michael-Michael-Aldol reaction.

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Related Publications:

1 "Organocatalytic synthesis of spiro compounds via a cascade Michael-Michael-Aldol reaction" X. Companyó, A. Zea, A.-N. R. Alba, A. Mazzanti, A. Moyano and R. Rios*. Chem. Commun. 2010, 46, 6953-6955.

2 "Highly stereoselective synthesis of spiropyrazolones" A. Zea, A.-N. R. Alba, G. Valero, T. Calbet, M. Font-Bardía, A. Moyano, R. Rios*. Eur. J. Org. Chem. 2011, 1318-1334.

3 “Highly enantioselective cascade synthesis of spiropyrazolones” A. Zea, A.-N. R. Alba, A. Mazzanti, A. Moyano, R. Rios*, Org. Biomol. Chem. 2011, 9, 6519-6523.

Related research groups

Organic Chemistry: Synthesis, Catalysis and Flow

Key Publication

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