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Synlett 1997; 1997(3): 291-292
DOI: 10.1055/s-1997-767
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Asymmetric C-C Bond Forming Reactions by Chiral Crown Catalysts; Darzens Condensation and Nitroalkane Addition to the Double Bond

Péter Bakó1 , Áron Szöllõsy2 , Petra Bombicz3 , László Tõke4
  • 1Department of Organic Chemical Technology, Technical University of Budapest, H-1521 Budapest, P.O. Box 91, Hungary, Fax: 36-1 463 3648, Email: P-Bako@ch.bme.hu
  • 2NMR Laboratory of the Institute for General and Analytical Chemistry, Technical University of Budapest, H-1521 Budapest, Szt. Gellért tér 4, Hungary
  • 3Central Research Institute for Chemistry, Hung. Acad. of Sci., P.O.Box 17, H-1525 Budapest, Hungary
  • 4Department of Organic Chemical Technology, Technical University of Budapest, H-1521 Budapest, P.O. Box 91, Hungary, Fax: 36-1 463 3648
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Publication History

Publication Date:
31 December 2000 (online)

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A new, efficient crown ether 1 anellated to a sugar derivative has been prepared which shows significant asymmetric induction as phase transfer catalyst in the Michael addition of 2-nitropropane to chalcone (60% ee for the S antipode) and in the Darzens condensation of phenacyl chloride and benzaldehyde (64% ee), simultaneously changing the PT process from solid-liquid to liquid-liquid phase.

chiral crown ethers - asymmetric Michael addition - Darzens condensation