Organocatalytic access to enantioenriched spirooxindole-based 4-methyleneazetidines

Giulia Rainoldi; Matteo Faltracco; Claudia Spatti; Alessandra Silvani; Giordano Lesma

doi:10.3390/molecules22112016

Organocatalytic access to enantioenriched spirooxindole-based 4-methyleneazetidines

Giulia Rainoldi, Matteo Faltracco, Claudia Spatti, Alessandra Silvani^*, Giordano Lesma

^*Corresponding author for this work

Research output: Contribution to Journal › Article › Academic › peer-review

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.

Original language	English
Article number	2016
Journal	Molecules
Volume	22
Issue number	11
DOIs	https://doi.org/10.3390/molecules22112016
Publication status	Published - 1 Nov 2017

Keywords

Azetidines
Cinchona-based catalysts
Organocatalysis
Spirooxindoles

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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title = "Organocatalytic access to enantioenriched spirooxindole-based 4-methyleneazetidines",

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.",

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T1 - Organocatalytic access to enantioenriched spirooxindole-based 4-methyleneazetidines

AU - Rainoldi, Giulia

AU - Faltracco, Matteo

AU - Spatti, Claudia

AU - Silvani, Alessandra

AU - Lesma, Giordano

PY - 2017/11/1

Y1 - 2017/11/1

N2 - 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.

AB - 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.

KW - Azetidines

KW - Cinchona-based catalysts

KW - Organocatalysis

KW - Spirooxindoles

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Organocatalytic access to enantioenriched spirooxindole-based 4-methyleneazetidines

Abstract

Keywords

UN SDGs

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