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Tertiary Amine-Catalyzed Chemoselective and Asymmetric [3 + 2] Annulation of Morita–Baylis–Hillman Carbonates of Isatins with Propargyl Sulfones

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posted on 02.09.2011, 00:00 authored by Jing Peng, Xin Huang, Lin Jiang, Hai-Lei Cui, Ying-Chun Chen
A chemo- and enantioselective [3 + 2] annulation of Morita–Baylis–Hillman carbonates of isatins with propargyl sulfones was catalyzed by a β-ICD O-MOM ether 1c, affording spirocyclic 2-oxindoles bearing an unusual cyclopentadiene motif in outstanding ee values (up to >99%). More electrophiles, such as N-phenylmaleimide, have been also utilized to deliver complex spirocyclic 2-oxindoles with good results.