4.8 Article

Organocatalytic Enantioselective γ-Aminoalkylation of Unsaturated Ester: Access to Pipecolic Acid Derivatives

Journal

ORGANIC LETTERS
Volume 15, Issue 19, Pages 5028-5031

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol402358k

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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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The direct gamma-carbon functionalization of alpha,beta-unsaturated esters via N-Heterocyclic Carbene (NHC) catalysis is disclosed. This catalytically generated nucleophilic gamma-carbon undergoes highly enantioselective additions to hydrazones. The resulting delta-lactam products can be readily transformed to optically enriched pipecolic acid derivatives.

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