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

LD Harris, RL Jenkins, NCO Tomkinson

Index: Harris, Lisa D.; Jenkins, Robert L.; Tomkinson, Nicholas C.O. Tetrahedron Letters, 2005 , vol. 46, # 10 p. 1627 - 1629

Full Text: HTML

Citation Number: 6

Abstract

The enantiomeric excess observed for the exo-adduct from the Lewis acid catalysed Diels– Alder reaction between cyclopentadiene and methacrolein can be increased up to 21% by simple modification of the electronics of the aromatic 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 density on the aromatic ring.