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. 2019 Apr 5;84(7):4009-4016.
doi: 10.1021/acs.joc.8b03270. Epub 2019 Mar 21.

Diastereoselective ABB' Three-Component Synthesis of Highly Functionalized Spirooxindoles Bearing Five Consecutive Asymmetric Carbons

Thavaraj Vivekanand  1 , B S Vachan  1 , Muthu Karuppasamy  1 , Isravel Muthukrishnan  1 , C Uma Maheswari  1 , Subbiah Nagarajan  2 , Nattamai Bhuvanesh  3 , Vellaisamy Sridharan  1   4
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Diastereoselective ABB' Three-Component Synthesis of Highly Functionalized Spirooxindoles Bearing Five Consecutive Asymmetric Carbons

Thavaraj Vivekanand et al. J Org Chem. .

Abstract

The synthesis of spirooxindoles bearing tetrahydro-4 H-cyclopenta[ b]furan framework was established starting from isatin-derived aldehydes and 2 equiv of 1,3-dicarbonyl compounds involving a piperidine-catalyzed ABB' three-component domino process. This reaction was highly diastereoselective affording a single diastereomer of spirooxindoles with five consecutive asymmetric carbons including spiro and tetrasubstituted carbon centers. In addition, this waste-free (-2H2O) reaction showed high atom economy and step economy by creating four new bonds, including three C-C bonds and one C-O bond, and two rings (one carbo- and one heterocyclic) in a single operation. The mechanism of this three-component domino process involved sequential Knoevenagel condensation-Michael addition-intramolecular oxa-Michael addition-intramolecular aldol reactions.

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