4.8 Article

Highly Enantioselective Addition of Enals to Isatin-Derived Ketimines Catalyzed by N-Heterocyclic Carbenes: Synthesis of Spirocyclic γ-Lactams

Journal

ORGANIC LETTERS
Volume 14, Issue 21, Pages 5412-5415

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol302475g

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Funding

  1. Singapore National Research Foundation (NRF)
  2. Singapore Economic Development Board (EDB)
  3. GlaxoSmithKline (GSK)
  4. Nanyang Technological University (NTU)

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An N-heterocyclic carbene (NHC)-catalyzed annulation reaction of isatin N-Boc ketimines and enals is developed for the synthesis of spirocyclic oxindole-gamma-lactams bearing one quaternary chiral center in good yields and excellent stereoselectivities (up to >20:1 dr and 99% ee).

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