4.8 Article

Trans-Stereoselectivity in the Reaction between Homophthalic Anhydride and Imines

Journal

ORGANIC LETTERS
Volume 10, Issue 21, Pages 4759-4762

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol801757r

Keywords

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Funding

  1. UPV/EHU-GV/EJ [IT-324-07]
  2. Spanish MEC [CTQ2007-67528, CSD 2007-00006]
  3. European Social Fund

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The reaction between homophthalic anhydride and imines in the presence of Ticl(4) and diisopropyl ethyl amine is trans-selective. Under these conditions, the reaction using homochiral imines can be highly diastereoselective, thus allowing the synthesis of enantiopure 1,2,3,4-tetrahydro-1-oxoquinoline-4-carboxylic acids.

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