engleski

Construction of tetrasubstituted centers of chirality in isoindolinones via Brønsted acid catalysis

Isoindolinones have attracted much attention among synthetic chemists, as they are integral structural parts of a number of natural products and biologically active compounds. In most cases, only a single enantiomer is effective, or has a better activity profile than the other. Consequently, the synthesis of these structural motifs and the natural products that contain them has been the subject of much elegant and effective research. The most straightforward way to functionalize isoindolinones includes transformations of easily accessible 3- hydroxyisoindolinone precursors. Their ability to form highly reactive species under mild conditions renders them as an attractive substrates in various catalytic reactions. The overview of our recent achievements in the construction of isoindolinone derivatives comprising tetrasubstituted centers of chirality will be presented. The focus will be given on chiral Brønsted acid-catalyzed additions of aromatic and non-aromatic carbon nucleophiles to in situ generated isoindolinone-derived ketimines for the construction of titled compounds. Generally, the transformations proceed smoothly and the corresponding products are isolated predominantly in high yields and enantioselectivities.

chirality ; Brønsted acid catalysis

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