Effects of Water Addition on a Catalytic Fluorination of Dienamine.

We investigate the effects of water addition on a highly stereocontrolled fluorination of dienamine generated by α-branched enals and 6'-hydroxy-9-amino-9-deoxy--quinidine with -fluorobenzenesulfonimide (NFSI) in the presence of Brønsted acid both experimentally and theoretically. It is experimentally found that water addition to organic solvent significantly shortens the reaction time whereas excessive water addition decreases the enantiomeric excess. The results calculated with three-dimensional reference interaction site model self-consistent field (3D-RISM-SCF) method are in good agreement with the experimental ones.