Organocatalytic enantioselective decarboxylative reaction of malonic acid half thioesters with cyclic N-sulfonyl ketimines by using N-heteroarenesulfonyl cinchona alkaloid amides

Shuichi Nakamura, Masahide Sano, Ayaka Toda, Daisuke Nakane, Hideki Masuda

Research output: Contribution to journalArticlepeer-review

80 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)3929-3932
Number of pages4
JournalChemistry - A European Journal
Volume21
Issue number10
DOIs
Publication statusPublished - 7 Oct 2014

Keywords

  • Enantioselectivity
  • Mannich reaction
  • Organocatalysis
  • Quaternary stereocenters

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