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

Harris, Lisa D. and Jenkins, Robert L. and Tomkinson, Nicholas C. O. (2005) The modulation of face-face π-π interactions in Lewis acid catalysis. Tetrahedron Letters, 46 (10). pp. 1627-1629. ISSN 0040-4039

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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.

ORCID iDs

Harris, Lisa D., Jenkins, Robert L. and Tomkinson, Nicholas C. O. ORCID logoORCID: https://orcid.org/0000-0002-5509-0133;