This work describes the synthesis of enantioenriched spiro compounds, incorporating the azetidine and the oxindole motifs. The preparation relies on a formal [2 + 2] annulation reaction of isatin-derived N-tert-butylsulfonyl ketimines with allenoates. The asymmetric induction is secured by an organocatalytic strategy, exploiting a bifunctional cinchona-type β-isocupridine-based catalyst. Some post-transformation products, including unexpected spiropyrroline and 3,3-disubstituted oxindole derivatives, are also presented.
Organocatalytic access to enantioenriched spirooxindole-based 4-methyleneazetidines / G. Rainoldi, M. Faltracco, C. Spatti, A. Silvani, G. Lesma. - In: MOLECULES. - ISSN 1420-3049. - 22:11(2017 Nov 21).
Organocatalytic access to enantioenriched spirooxindole-based 4-methyleneazetidines
G. RainoldiPrimo
;A. Silvani
Penultimo
;G. LesmaUltimo
2017
Abstract
This work describes the synthesis of enantioenriched spiro compounds, incorporating the azetidine and the oxindole motifs. The preparation relies on a formal [2 + 2] annulation reaction of isatin-derived N-tert-butylsulfonyl ketimines with allenoates. The asymmetric induction is secured by an organocatalytic strategy, exploiting a bifunctional cinchona-type β-isocupridine-based catalyst. Some post-transformation products, including unexpected spiropyrroline and 3,3-disubstituted oxindole derivatives, are also presented.File | Dimensione | Formato | |
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