4.8 Article

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

Journal

ORGANIC LETTERS
Volume 13, Issue 17, Pages 4584-4587

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol201776h

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Funding

  1. National Natural Science Foundation of China [20972101, 21021001]
  2. National Basic Research Program of China (973 Program) [2010CB-833300]

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A chemo- and enantioselective [3 + 2] annulation of Morita-Baylis-Hillman carbonates of isatins with propargyl sulfones was catalyzed by a beta-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.

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