title: Origins of aryl substituent effects on the stereoselectivities of additions of silyl enol ethers to a chiral oxazolinium ion.
abstract: Density functional theory calculations are reported that reveal the role of aromatic interactions in the additions of aryl-substituted silyl enol ethers to a chiral oxazolinium ion. Aryl-substituted silyl enol ethers give the opposite diastereomer of the adduct than do aliphatic silyl enol ethers, due to a combination of attractive cation-π and CH-π interactions, reduced steric repulsion, and lower torsional strain in the more "crowded" transition state.
authors: School of Chemistry, University of Melbourne, Victoria 3010, Australia. ekrenske@unimelb.edu.au
authors: Elizabeth H
authors: EH
authors: Krenske