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Issue 77, 2016
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Highly diastereoselective entry into chiral spirooxindole-based 4-methyleneazetidines via formal [2+2] annulation reaction

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Abstract

A diastereoselective, DABCO-catalyzed reaction of isatin-derived ketimines with allenoates is described. Exploiting the stereodirecting effect of the bulky tert-butanesulfinyl chiral auxiliary, the method provides an efficient access to single diastereoisomers of unprecedented spirocyclic oxindoles, bearing a 4-methyleneazetidine ring at the spiro junction. The versatility of the method is fully demonstrated by further transformations including the conversion to relevant spirocyclic oxindolo-β-lactams.

Graphical abstract: Highly diastereoselective entry into chiral spirooxindole-based 4-methyleneazetidines via formal [2+2] annulation reaction

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Publication details

The article was received on 15 júl. 2016, accepted on 25 ágú. 2016 and first published on 26 ágú. 2016


Article type: Communication
DOI: 10.1039/C6CC05838H
Chem. Commun., 2016,52, 11575-11578
  • Open access: Creative Commons BY-NC license
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    Highly diastereoselective entry into chiral spirooxindole-based 4-methyleneazetidines via formal [2+2] annulation reaction

    G. Rainoldi, M. Faltracco, L. Lo Presti, A. Silvani and G. Lesma, Chem. Commun., 2016, 52, 11575
    DOI: 10.1039/C6CC05838H

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