Stereochemical outcomes of C–F activation reactions of benzyl fluoride

• Neil S. Keddie,
• Pier Alexandre Champagne,
• Justine Desroches,
• Jean-François Paquin and
• David O'Hagan

Beilstein J. Org. Chem. 2018, 14, 106–113, doi:10.3762/bjoc.14.6

• demonstrated that both associative and dissociative pathways operate to varying degrees, according to the nature of the nucleophile and the hydrogen bond donor. Keywords: benzylic fluorides; C–F activation; chiral liquid crystal; 2H NMR; PBLG; stereochemistry; Introduction The C–F bond is the strongest

• with the electric field gradients associated with the orientated media, creating anisotropy and resolving into two sets of doublets. If there is sufficient resolution between these quadrupolar couplings, then the enantiomeric ratio can be recorded. We have used poly-γ-benzyl-L-glutamate (PBLG

• reduced under Noyori’s conditions [12] using (S,S)-Ru(DPEN)2 as catalyst and [2H2]-formic acid as the deuterium source. This afforded the corresponding 7-[2H1]-(S)-benzyl alcohol ((S)-3) in moderate yield (81%) and high ee (95%), as evidenced by 2H-PBLG-NMR. Benzyl alcohol 3 was converted to the