Highly Diastereo-, α-Regioselective Catalyst-Free Construction of Adjacent Dispirobisoxindoles with Three Contiguous Quaternary Carbon Centers

^§ These two authors contributed equally to this work

Abstract

A new methodology was developed for the highly diastereoselective construction of dispirobisoxindole scaffolds via a domino α-regioselective Michael/cyclization reaction sequence of 3-isothiocyanato oxindoles and isatylidene malononitriles under catalyst-free conditions. Complex polycyclic oxindoles featuring two side-by-side oxindole skeletons and three contiguous quaternary carbon centers were synthesized in up to 95% yield and >20:1 dr. This protocol could provide libraries of stereochemically rich small molecules that will help in the search for new bioactive molecules.

Key words

3-isothiocyanato oxindoles - quaternary carbon center - diastereoselective - α-regioselective - catalyst-free

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