Catalyst-Free Ring Opening of Spiroaziridine Oxindoles by Heteronucleophiles: An Approach to the Synthesis of Enantiopure 3-Substituted Oxindoles.

Abstract

A simple catalyst-free method was developed for the ring opening of spiroaziridine oxindoles by three different nucleophiles, namely, amines, thiols, and methanol, to produce enantiopure (up to 99%) vicinal diaminooxindoles, β-aminosulfides, and β-amino-3-methoxyoxindole, respectively, in good to excellent yields. In contrast to the spiroepoxides, spiroaziridines are opened regio- and stereospecifically through the pseudobenzylic spirocenter under catalyst-free conditions. Moreover, unlike simple 2-substituted aziridines, these spiroaziridines are opened up with retention in configuration at the C3-spirocenter.