five

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

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NIAID Data Ecosystem2026-03-11 收录
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https://figshare.com/articles/dataset/Diastereoselective_ABB_Three-Component_Synthesis_of_Highly_Functionalized_Spirooxindoles_Bearing_Five_Consecutive_Asymmetric_Carbons/7877855
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The synthesis of spirooxindoles bearing tetrahydro-4H-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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2019-03-21
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