4.7 Article

Asymmetric Synthesis of Spirooxindole δ-Lactones with Vicinal Tertiary and Quaternary Stereocenters via Regio-, Diastereo-, and Enantioselective Organocatalytic Vinylogous Aldol-cyclization Cascade Reaction

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 359, Issue 22, Pages 4043-4049

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201701104

Keywords

Organocatalysis; 3-Akylidene oxindoles; Spirooxindole delta-lactones; Vinylogous aldol - cyclization

Funding

  1. Ministry of Science and Technology, Taiwan [106-2113-M-033-006-MY2]

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A highly region-, diastereo-, and enantioselective organocatalytic vinylogous aldol-cyclization cascade reaction of prochiral 3-akylidene oxindoles to isatins has been achieved by using bifuctional organocatalysts. A variety of enantioenriched spirooxindole -lactones with vicinal tertiary and quaternary stereocenters were generated in good to excellent yields with good to high diastereoselectivities and enantioselectivities.

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