The modulation of face-face π-π interactions in Lewis acid catalysis

Lisa D. Harris, Robert L. Jenkins, Nicholas C. O. Tomkinson

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The enantiomeric excess obsd. for the exo-adduct from the Lewis acid catalyzed Diels-Alder reaction between cyclopentadiene and methacrolein can be increased up to 21% by simple modification of the electronics of the arom. ring in a series of stilbene-derived diol ligands, suggesting that the proposed face-face π-π interaction between the catalyst and the dienophile can be modulated by altering the electron d. on the arom. ring.
Original languageUndefined/Unknown
Pages (from-to)1627-1629
Number of pages3
JournalTetrahedron Letters
Volume46
Issue number10
DOIs
Publication statusPublished - 2005

Keywords

  • methacrolein
  • dienophile
  • aromatic rings

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