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- Title
Effects of Water Addition on a Catalytic Fluorination of Dienamine.
- Authors
Kuraoku, Daiki; Yonamine, Tsunaki; Koja, Genta; Yoshida, Norio; Arimitsu, Satoru; Higashi, Masahiro; Shibata, Norio
- Abstract
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-epi-quinidine with N-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. It is revealed that the shortness of reaction time is caused by the reactant destabilization and that the decrease in enantiomeric excess is due to the difference of hydration free energy between two transition states.
- Subjects
FLUORINATION; BRONSTED acids; WATER
- Publication
Molecules, 2019, Vol 24, Issue 19, p3428
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules24193428