4.7 Article

Diastereo- and Enantioselective [3+2] Cycloaddition Reaction of Morita-Baylis-Hillman Carbonates of Isatins with N-Phenylmaleimide Catalyzed by Me-DuPhos

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 8, Pages 4143-4147

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo3002535

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Funding

  1. National Natural Foundation of China
  2. Ministry of Science and Technology [2011CB808600]
  3. Chinese Academy of Sciences

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A Me-DuPhos-catalyzed efficient asymmetric [3 + 2] cycloaddition reaction between Morita-Baylis-Hillman carbonates of isatins and N-phenylmaleimide has been developed. This reaction constructs three chiral centers in one step to afford spirocyclopentaneoxindoles in good yields (up to 84%) with excellent diastereo- and enantioselectivies (up to 99% ee).

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