Chiral, non-racemic, distally-bridged resorcin[4]arenes as models for use in asymmetric processes

Gareth Arnott, Philip C. Bulman Page, Harry Heaney, Roger Hunter, Edward P. Sampler

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The synthesis of enantiomerically pure, distally-bridged resorcinarenes 3 with various R groups (CH3, C5H11, C-11 H-23) is reported. The key step makes use of the Mannich reaction for attachment of a chiral diamine-line 2 across the cavity. Yields for this step are good to excellent. One of the bridged compounds exhibits modest activity (27% ee) as an enantioselective catalyst in the addition of diethylzinc to benzaldehyde.
Original languageEnglish
Pages (from-to)412-414
Number of pages3
JournalSynlett
Volume3
DOIs
Publication statusPublished - 2001

Keywords

  • bridged resorcin[4]arene
  • ACID
  • ALKYLATION
  • chiral resorcin[4]arene.
  • CALIXARENES
  • Mannich reaction
  • RESORCARENES
  • enantioselective catalyst
  • RING
  • C-2v-symmetric diamine chiral auxiliary
  • CALIX<4>RESORCINARENE DERIVATIVES
  • SELECTIVE DERIVATIZATION
  • CLOSURE
  • RESORCINOL
  • ALDEHYDES

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