Synthesis of d-mannitol-based crown ethers and their application as catalyst in asymmetric phase transfer reactions

Tamás Nemcsok, Zsolt Rapi, G. Keglevich, A. Grün, P. Bakó

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7 Citations (Scopus)

Abstract

A few new d-mannitol-based monoaza-15-crown-5 type chiral lariat ethers and 18-crown-6 type macrocycles were synthesized. These crown compounds were used as phase transfer catalysts in asymmetric Michael addititons and in a Darzens condensation under mild conditions to afford the corresponding products in a few cases in good to excellent enantioselectivities. In the Michael addition of diethyl acetoxymalonate to trans-chalcone, in the addition of diethyl acetamidomalonate to ß-nitrostyrene, in the reaction of diethyl bromomalonate with benzylidene malononitriles, in the cyclopropanation reaction of diethyl bromomalonate and 2-benzylidene-1,3-indandione, and in the Darzens condensation of α-chloroacetophenone with benzaldehyde, maximum enantioselectivities of 39%, 65%, 99%, 56%, and 62%, respectively, were obtained in the presence of the d-mannitol-based macrocycles as the catalysts.

Original languageEnglish
Pages (from-to)407-419
Number of pages13
JournalChirality
Volume30
Issue number4
DOIs
Publication statusPublished - Apr 1 2018

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Keywords

  • asymmetric Michael addition
  • Darzens condensation
  • phase transfer catalysis
  • sugar-based crown ethers

ASJC Scopus subject areas

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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