4.6 Article

Organocatalytic Enantioselective Decarboxylative Reaction of Malonic Acid Half Thioesters with Cyclic N-Sulfonyl Ketimines by Using N-Heteroarenesulfonyl Cinchona Alkaloid Amides

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 10, Pages 3929-3932

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201406270

Keywords

enantioselectivity; Mannich reaction; organocatalysis; quaternary stereocenters

Funding

  1. MEXT [26105727]
  2. Grants-in-Aid for Scientific Research [26410117, 25109523, 26105727] Funding Source: KAKEN

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The organocatalytic enantioselective decarboxylative Mannich reaction of malonic acid half thioesters (MAHTs) with cyclic N-sulfonyl ketimines by using N-heteroarenesulfonyl cinchona alkaloid amides afforded products with high enantioselectivity. Both enantiomers of the products could be obtained by using pseudoenantiomeric chiral catalysts. The reaction proceeds through a nucleophilic addition of the MAHTs to the ketimines prior to decarboxylation.

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