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

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 ex...

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Veröffentlicht in:Journal of organic chemistry 2018-04, Vol.83 (7), p.3633-3644
Hauptverfasser: Hajra, Saumen, Singha Roy, Somnath, Biswas, Anurag, Saleh, Sk Abu
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b03288