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Molecules 2017, 22(11), 2016;

Organocatalytic Access to Enantioenriched Spirooxindole-Based 4-Methyleneazetidines

Department of Chemistry, University of Milan, via Golgi 19, 20133 Milan, Italy
Department of Chemistry & Pharmaceutical Sciences, Amsterdam Institute of Molecules Medicines & Systems (AIMMS), Vrije Universiteit Amsterdam, De Boelelaan 1108, 1081 HZ Amsterdam, The Netherlands
Author to whom correspondence should be addressed.
Received: 30 October 2017 / Revised: 15 November 2017 / Accepted: 17 November 2017 / Published: 21 November 2017
(This article belongs to the Special Issue Advances in Spiro Compounds)
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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. View Full-Text
Keywords: spirooxindoles; organocatalysis; azetidines; cinchona-based catalysts spirooxindoles; organocatalysis; azetidines; cinchona-based catalysts

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Rainoldi, G.; Faltracco, M.; Spatti, C.; Silvani, A.; Lesma, G. Organocatalytic Access to Enantioenriched Spirooxindole-Based 4-Methyleneazetidines. Molecules 2017, 22, 2016.

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