Enantioselective Michael addition of 2-nitropropane to chalcone analogues catalyzed by chiral azacrown ethers based on α-D-glucose and D-mannitol

Tibor Bakó, Péter Bakó, György Keglevich, Nikoletta Báthori, Mátyás Czugler, János Tatai, Tibor Novák, Gyula Parlagh, László Toke

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Abstract

The chiral monoaza-15-crown-5 type lariat ethers 1 and 2 derived from α-D-glucose and from D-mannitol, respectively, have been applied as phase transfer catalysts in the enantioselective Michael addition of 2-nitropropane to aromatic 3b-c and heteroaromatic 3d-h chalcone analogues. Among the catalysts, the glucose-based 1c with a phosphinoxidobutyl side arm proved to be the most effective, it inducing 34% e.e. for 4b, 59% e.e. for 4c, 80% e.e. for 4d, 64% e.e. for 4e, 17% e.e. for 4f. Catalyst 1a having 3-hydroxypropyl substituent resulted in 81% e.e. for compound 4g. The formation of the (+)-(S)-enantiomer of 4 was preferred using crown ethers 1a-c, while the (-)-(R)-enantiomer was in excess with catalyst 2. The absolute configuration of the Michael adduct 4d was determined by single-crystal X-ray analysis.

Original languageEnglish
Pages (from-to)1917-1923
Number of pages7
JournalTetrahedron Asymmetry
Volume14
Issue number13
DOIs
Publication statusPublished - Jul 4 2003

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ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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