High pressure chiral recognition experiments - A route to homochiral 4-fluorocyclohexenones

4-Fluorocyclohexadienones, prepared by an improved Jacquesy-process, were shown to undergo highly face-selective Diels-Alder reactions with the homochiral cyclopentadiene 1. Some of the diastereoselective transformations, quite unique rearrangements of ?-hydroxy compounds resulting from nucleophilic attack to the carbonyl group as well as selected Retro-Diels-Alder reactions, are reported.DFGFonds der Chemischen Industri