Beilstein Journal of Organic Chemistry 2015-01-01

Bifunctional phase-transfer catalysis in the asymmetric synthesis of biologically active isoindolinones.

Antonia Di Mola, Maximilian Tiffner, Francesco Scorzelli, Laura Palombi, Rosanna Filosa, Paolo De Caprariis, Mario Waser, Antonio Massa

Index: Beilstein J. Org. Chem. 11 , 2591-9, (2015)

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Abstract

New bifunctional chiral ammonium salts were investigated in an asymmetric cascade synthesis of a key building block for a variety of biologically relevant isoindolinones. With this chiral compound in hand, the development of further transformations allowed for the synthesis of diverse derivatives of high pharmaceutical value, such as the Belliotti (S)-PD172938 and arylated analogues with hypnotic sedative activity, obtained in good overall total yield (50%) and high enantiomeric purity (95% ee). The synthetic routes developed herein are particularly convenient in comparison with the current methods available in literature and are particularly promising for large scale applications.